GB2068948A

GB2068948A - 2-nitro-5-(substituted phenoxy) benzoyl derivatives as herbicides

Info

Publication number: GB2068948A
Application number: GB8102466A
Authority: GB
Original assignee: Mobil Oil Corp
Current assignee: ExxonMobil Oil Corp
Priority date: 1980-02-01
Filing date: 1981-01-27
Publication date: 1981-08-19
Also published as: GB2068948B; DD157992A5; IL62019A0; PT72432B; PL131421B1; CS221821B2; PT72432A; AU6651581A; EP0034883A1; ES8201116A1; PL229481A1; JPS56127335A; ES498957A0; CS221819B2; DK41181A; GR72986B; CS221820B2; ZA81649B; BR8100596A

Description

1

GB 2 068 948 A 1

SPECIFICATION

2-nitro-5-(substituted Phenoxy) Benzoyl Derivatives as Herbicides

This invention is concerned with herbicidal 2-nitro-5-(substituted-phenoxy) benzoyl derivatives.

United States Patent Nos. 3,652,645; 3,784,635; 3,873,302; 3,983,168 and 3,907,866 describe certain phenoxy benzoic acid derivatives which are useful as herbicides. We have now found 5 further phenoxy benzoic acid derivatives which are useful as herbicides.

This invention provides certain herbicidal compounds falling within the general formula:

0

ii x-j c-qa o)— 0 —(o)—tf02 (I)

x2

wherein X, is halogen, X2 is selected from halogen and hydrogen, and Z is a polyhalo,^ alkyl1_4 group 10 such as CF3, CHF2, C4F9, CF2CH2CH3 and CH2CI. Preferably, X, is chloro, Z is CF3and X2 is hydrogen. QA 10 in the formula includes certain groups more fully described below.

The specific 2-nitro-5-(substituted-phenoxy) benzoyl compounds are described below. One method for preparing these compounds is the use of the Ullmann ether synthesis reaction between the alkali metal (e.g., Na, K) salt of a suitable substituted phenol, e.g., m-hydroxy benzoic acid or m-cresol 15 with an active halogen-substituted aromatic, e.g., 3,4-dichlorobenzotrifluoride. The intermediate 15

obtained may be nitrated and the desired final derivatives subsequently prepared by known procedures to the desired benzoyl compound. Where m-cresol is used as a starting material, the product obtained can be oxidized and subsequently nitrated before the derivative is prepared.

A. Substituted Phenyl Esters, Phenylthio Ester, Substituted Phenylthio Esters

20 Illustrative compounds of this class are those of the formula: 20

II

■ c1

cf3 -(o^- ° ~(0/

no 2

(II)

Where Q is 0 or S, n is an integer from 1 to 5, and X is selected from N02; lower alkyl or C.,_4;

halogen; phenyl; COOR where P. is lower alkyl of C1-4, H or a cation selected from alkali metals, alkaline earth metals, ammonium and lower alkyl and di-lower alkyl ammonium; CN; lower alkyl thio of C^; 25 lower alkoxy of C^; trifluoromethyl; and combinations thereof. X can be hydrogen when Q is sulfur. 25

Compound 1

Preparation of 2,4-dinitro-6-sec-butylphenyl 5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzoate.

To a stirred solution of 2,4-dinitro-6-sec-butylphenyl (3.60 g, 0.015 mole) and 5-[2-chloro-4-30 (trifluoromethy!)phenoxy]-2-nitrobenzoyl chloride (5.68 g, 0.015 mole) in toluene (25 ml) was added 30 triethylamine (1.50 g, 0.015 mole). The temperature exothermed to 45°C and there was an immediate precipitation of triethylamine hydrochloride. The reaction was stirred and heated to 110°F for 15 hours. The precipitate was filtered from the cooled solution, washed and dried to give triethylamine hydrochloride (1.8 g). The toluene solution was washed with 10% sodium hydroxide (3x25 ml). The 35 toluene was then stripped off a rotary evaporator to give 5.5 g (62%) of a crude brown oil which slowly 35 crystallized. Recrystallization from methanol gave 2.1 g of an off white solid, m.p. 109—110°C. I.R.

(nujol): C=0,1765 cm-1.

NMR (D6 Acetone):

triplet 0.9 ppm (3H, J=3.5 Hz);

40 doublet 1.37 ppm (3H, J=3.5 Hz); 40

multiplet 1.82 ppm (2H);

multiplet 3.35 ppm (1H);

multiplet 7.5—8.2 (5H);

doublet 8.45 ppm (1H, J=4.5 Hz);

45 doublet 8.82 ppm (1H, J=1.2 Hz); 45

doublet 9.02 ppm (1H, J=1.2 Hz).

In a similar manner the following compounds were prepared as defined according to Formula II:

2

GB 2 068 948 A 2

Phenyl Substitution

10

15

20

25

Compound

(OorS)

m.p., °C

2

0

2-N02

137—9

3

0

3-N02

93.5

4

0

4-N02

115—7

5

0

5-CH3-2N02

88—90

6

0

2-CI-4N0.,

99—101

7

0

4-CI

135—7

8

0

4-Cl-2CH3

121—2

9

0

2-CI-4-CH3

105—7

10

0

2-CI-4-phenyl

128—30

11

0

2,4-(CI)2

144—7

12

0

4-COOCH,

103—6

13

0

4-CN

103—5

14

0

4-SCH3

94—5

15

0

3-OCH3

95—7

16

0

4-0CH3

128—9

17

0

3-CF3

oil

18

0

4-COONa

215—20

19

0

4-C00H

191—8

20

s

H

oil

21

s

4-CI

128—30

22

s

4-CH3

90—3

23

s

4-OCH3

oil

24

s

3,4-(CI)2

oil

10

15'

20

25

Other compounds of this class include:

30

35

Compound

2,6-diethylphenyl 5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzoate S-[2-carboxyphenyl) 5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzenecarbothioate 4-cyano-2,6-dibromophenyl 5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzoate (m.p. 30

170—1 °C IR. C=0 1775 cm"1)

3,6-dichloro-2-methoxycarbonylphenyl 5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzoate (2,6-di-6-butyl)phenyl 5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzoate (oil I.R. C=0 1752 cm-1)

pentachlorophenyl 5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzoate. 35

B. Heterocyclic Esters

Illustrative compound of this class are those of the formula:

0

u

.CL

Ch o

o

Het

NO'

(III)

40

45

50

55

where Q is 0 or S and Het is a substituted or unsubstituted heterocyclic ring of 5 to 7 members comprising carbon in combination with one or more of sulfur, oxygen and nitrogen where a carbon atom on the ring is bound directly to Q.

Compound 25

Preparation of 3-pyridyl 5 [2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzoate:To a stirred solution of 5-[2-chloro-4-(trifluoromethy!)phenoxy]-2-nitrobenzoyl chloride (3.79 g, 0.01 mole) and triethyl amine (1.01 g, 0.01 mole) in toluene (50 ml) was added 3-hydroxypyridine (0.95 g, 0.01 mole). The temperature exothermed to 33° and there was an immediate precipitate. The reaction was then refluxed for 24 hours, cooled to room temperature and the triethylamine hydrochloride precipitate collected by filtration. The toluene solution was washed with dilute sodium hydroxide solution and then with saturated sodium chloride solution. After drying and evaporation of the solvent there was obtained 3.1 g of brown oil which solidified. This was triturated with hexane and the solid filtered and dried to give a tan product, m.p. 65—68°C.

I.R. (nujol): C=0,1765 cm-1

NMR (D6-acetone):

complex multiplet 7.2—8.1 ppm (7H);

doublet 8.50 ppm (1H, J=4.5 Hz);

multiplet 8.75 ppm (2H).

40

45

50

55

3

GB 2 068 948 A 3

Compound 26

This compound is defined in accordance with Formula III as "Q" is 0 and ' Het is

■25

where n is 1 to 5 and X is selected from NOz, lower alkyl of halogen, phenyl, phenoxy, CN, lower alkyl thio of C^, lower alkoxy of C,^,, trifluoromethyl and combinations thereof;

10

The compound was prepared by the procedure shown for Compound 25. Compound 26 has an m.p. of S 153—161 °C.

Other compounds of this class include:

Compound

3-( 1,2,5 thiadiazoloyl)-5-[2-chloro-4-trifluoromethyl)phenoxy]-2-nitrobenzoate 1,2-dihydro-1,6-dimethyl-2-oxo 4-pyridinyl 5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-I'O nitrobenzoate

6-(2,3-dihydro-3-oxo-pyridazinyl) 5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzoate 2-chloro-6-pyridyl 5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzoate ' s-(2,6-dichloro-4-s-triazinyl) 5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzoate

S-(2-methyl 1,3,4-thiadiazol-5-yl) 5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-15 nitrobenzenecarbothioate 1 g

S-(2-pyridinyl) 5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzenecarbothioate N-oxide S-[4-methyl-3-thioxo-3H-1,2-dithiol-5-yl] 5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-

nitrobenzenecarbothioate S-[3,5-bis-(diethylamino)-s-triazinyl] 5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-20 nitrobenzenecarbothioate

0-[2-oxo-furan-3-yl-] 5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzene carboxylate (oil, I.R. C=0 1797 and 1750 cm"1).

C. Substituted C,_4 Alkyl Esters

Illustrative compounds of this class are those of the formula:

0 II

C-O-subsh alkyl ■] - 4

20

25

(IV)

wherein the substituents on the straight or branched C.,_4 alkyl group are selected from cyano; phenyl;

30

0 0

I! II

-C—R2; —0—C—R2 30

phenoxy; nitro; SR,; SOR,; S02R,; where R, is an alkyl of 1 to 3 carbons and R2 is an alkyl or alkenyl of up to 3 carbons and wherein one or more of said substituents can be attached to any one or more of the carbons on said straight or branched C,_4 alkyl group.

The compounds of this class may be prepared by the methods shown above or alternatively by 35 displacement of an active halogen (e.g., Haloalkyl X) with the salt of an acid, e.g., 35

AR—C—OK

The following substituted C,_4 alkyl esters as defined by Formula IV were prepared:

4

GB 2 068 948 A 4

Compound

27

28

29

30

31

Substituted Alkyl Group

—c(ch3)2cn —ch(ch3)cn

—ch2coch3

~ch2~~(0)

m.p. °C oil oil

83—5 oil oil

0

32

-CHZ—CH2—OC—CH=CH2 0 CH,—

oil

10

15

33

34

35

36

37

38

39

40

—CH2—CH2—OC—C=CH2 —CH2—CH2—CN

ch2-ch2-o—(p)

-CH2CH2-(0)

—ch,c(ch,),—no2

-ch2—ch2—sch3 -ch2—ch2—so2ch3

Other compounds of this class include:

20

25

30

—CH2CN

—CH2—C(OCH3)2 —CH

-ch,

,2—CH(CH3)—N02

-ch,—ch(0c,h

2' 5'2

-ch2—so—ch3

-CH2—CH2—SO—CHa

—CH,—S—CH,

oil oil

86—8

112—3

oily semisolid

I.R. C=0 1740 cm-1 oil

97—9

oil, I.R. C=0

1725 cm-1 m.p. 73—4° oil, I.R. C=0

1740 cm"1 1740 cm"1 115—8° I.R. C=0

1745 cm-1 113—5° I.R. C=0

1745 cm"1 oil I.R. C=0 1740 cm"1

Substituted Alkyl ch2—s—ch2ch3

ch2s—ch2ch3

0

1

ch2s—ch2ch3

I

0

Compound Name (ethylthio)methyl 5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitro-benzoate (ethylsulfinyl)methyl 5-[2-chloro -4-(trifluoromethyl)phenoxy]-2-nitro-benzoate

(ethylsulfonyl)methyl 5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzoate

10

15

20

25

30

35

CH3 0

CH—CCH,

1 -acetylethyl 5-l2-chloro-4-

trifluoromethyl)phenoxy]-2-nitro-benzoate

35

5

GB 2 068 948 A 5

Substituted Alkyl 0

ch2ch2ch2cch3

0

ch2ch2sch3

CH.

o

Compound Name

3-acetylpropyl

5-[2-chloro-4-(trifluoromethyl) ph enoxy] -2 -n itrob enzoate

2-(methylsulfinyl)ethyl

5-[2-chloro-4-(trifluoromethyl)-phenoxy]-2-nitrobenzoate

(3-fluorophenyl)methyl

5-[2-ch loro-4-(trif luoromethyl )-phenoxy]-2-nitrobenzoate (oil, I.R. C=0 1735 cm"1

o D. Carbonates and Thiocarbonates

Illustrative compounds of this class are those of the formula:

CF

(V)

10

15

20

25

where Q is 0 or S and Y is a straight or branched alkoxy, alkylthio, alkenyloxy or alkenylthio of 1 to 6 carbons, a dialkylamino of 2 to 6 carbons, or a heterocyclic amine such as morpholine.

Compound 41

Preparation of S-[(ethylthio)carbonyl] 5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzoate. To a stirred solution of 5-[2-chioro-4-(trifluoromethyl)phenoxy]-2-nitrobenozic acid (3.0 g, 0.0083 mole) in ether (15 ml) was added triethylamine (0.84 g, 0.0083 mole. A precipitate formed. The reaction was cooled to 4°C and a solution of ethylchlorothioformate (1.03 g, 0.0083 mole) in ether was added dropwise. Cooling was maintained during initial exotherm. The reaction was then stirred at room temperature for twenty hours. The precipitate of triethylamine hydrochloride was filtered. The ether was washed consecutively with 10% hydrochloric acid solution, 5% sodium hydroxide solution and water. The dried solution was evaporated to give 3.04 g of a yellow oil. I.R. (neat): C=0, 1675 and 1800 cm-1 NMR (CDCI3):

triplet 1.37 ppm (3H, J=3.5 Hz);

quartet 3.12 ppm (2H, J=3.5 Hz);

complex multiplet 7.0—8.0 ppm (5H);

doublet 8.15 ppm (1H, J=4.8 Hz).

In a similar manner, the following compounds as defined in accordance with formula V, were prepared:

10

15

20

25

30

•35

Compound

Q

Y

m.p., °C

42

0

och3

oil

43

0

och2ch3

oil

44

0

och2ch2ch3

oily semi-solid

45

0

och(ch3)2

oily semi-solid

46

0

och2ch2ch2ch3

oil

47

0

0ch2ch(ch,)2

oil

48

S

och3

oil

49

S

morpholino

137—8°

30

35

S-[(propylthio)thionocarbonyl] 5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzenecarbothioate is a further illustrative compound of this class wherein Q is S and Y is —SC3H7, as are the following compounds:

40

S S S S

y m.p., °C/I.R. cm 1

OC2H5

ch2—ch=ch2

0

oc3h7

och(ch3)2

oil, 1670 oil, 1672 oil, 1668 oil, 1740—1700

40

6

GB 2 068 948 A 6

E. Benzoyl Phosphonates

Illustrative compounds of this class are those of the formula:

0 0 II II

C— P—(OR 3 ) 2

o)— ° —(o)—no.

2 (VI)

where Ra is straight or branched alkyl of 1 to 6 carbons.

5 Compound 50 5.

Preparation of 5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzoyl-phosphonic acid,

diisopropyl ester.

To a stirred solution of 5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzoyl chloride (3.8 g, 0.01 mole) in ether (100 ml) was added triisopropyl phosphite (2.1 g, 0.01 mole). The reaction was 10 refluxed for one hour and the disappearance of phosphite monitored by v.p.c. The ether was stripped 10 off and the resulting oil placed under vacuum (1.0 ml) at 40°Cfortwo hours. The resulting amber liquid amounted to 5.2 g.

I.R. (neat): C=0, 1692 and 1730 cm-1 NMR (CDCIg):

15 doublet 1.29 ppm (3H,J=3.0 Hz); 15

doublet 1.37 ppm (3H, J=3.0 Hz);

multiplet 4.88 ppm (1H;

complex multipiet 6.9—8.0 ppm (5H);

broad doublet 8.37 ppm (1H, J=4.5 Hz).

20 In a similar manner, the following compound was prepared as an additional example of a benzoyl 20 phosphonate.

Compound 51

5-2-[chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzoyl-phosphonic acid diethyl ester was prepared and was an oil.

25 F. Substituted Alkanone Compounds 25

Illustrative compounds of this class are those of the formula:

0

ii

3 \W/ « \W/ N02

\ / I (vn)

where A is an alkyl of 1 to 3 carbons or hydrogen.

Compound 52

30 Preparation of 5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitropheny! ethanone (A is —CH3). 30

A stirred solution of 3-[2-chioro-4-(trifluoromethyl)phenoxy]phenyl ethanone (15.7 g, 0.05 mole) in dichloroethane (40 ml) was cooled to 0—5°C. Nitric acid (95%) (4.95 g, 0.075 mole) was added,

followed by the dropwise addition of 95% sulfuric acid (12.3 g, 0.125 mole) while maintaining the temperature below 5—10°C. Allowed reaction to warm to room temperature. The progress of the 35 reaction was monitored by v.p.c. The reaction solution was poured onto ice water and the organic 35"

solution separated, washed with water and dried. The solvent was evaporated to give 16 g of a brown oil, which was extracted with hot heptane. Upon cooling, the heptane solution furnished an oil fraction which solidifed to give 8.8 g of a brown solid, m.p. 58—60°C.

I.R. (nujol mull): C=0, 1710 cm"1; NOz, 1530 and 1315 cm"1.

40 Compound 53

5-[2-chloro-4-trifluoromethyl)phenoxy]-2-nitrobenzaldehyde ("A" is hydrogen in Formula VII) was prepared. It had a melting point of 99—100°C.

G. Amides

Illustrative compounds of this class include those of the formula:

7

GB 2 068 948 A 7

15

20

25

O

NO,

/

N

\0

(VIII)

wherein R4 is selected from hydrogen and straight or branched chain alkyl of 1—4 carbon; substituted or unsubstituted; R5 is selected from: phenyl;

10

(where n is 1 to 5 and X is selected from N02, lower alkyl of C1-4, halogen, phenyl or phenoxy), COOR (where R is lower alkyl of C1-4 or H or a cation), CN, lower alkyl thio of C,^, lower alkoxy of C,^, trifluoromethyl and combinations thereof; heterocyclicalkyl and heterocyclic, said heterocyclics of a 5 to 7 member ring comprising carbon in combination with one or more of sulfur, oxygen and nitrogen, hydroxyl, alkoxy of 1—3 carbons; —RBC02R6, where Re is an alkyl or alkenyl of up to 3 carbons; —R6CONH2;—R6CONHR2 or R6CON(R2)2; (where R2 is as defined above) alkoxy-alkyl where the alkoxy and alkyi may each contain a straight or branched C,3 alkyl chain; or where R4 and Rs together form a heterocyclic ring as hereinabove defined.

10

Compound 54

Preparation of N-phenyl 5-[2-chloro-4-(trifluoromethyl)phenoxyl]-2-nitrobenzamide.

To a stirred solution of 5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzoyl chloride (5.68 g, 0.015 mole) in toluene (35 ml) was added aniline (2.8 g, 0.30 mole). The temperature immediately rose to 45°C. The reaction was then heated to reflux for twelve hours. The cooled reaction was poured into dilute hydrochloric acid solution. The residual solids were filtered, washed with warm water and dried to give 4.1 g of a gray solid m.p. 190—4°C. Recrystallization from methanol gave 3.8 g, m.p. 191—4°C.

I.R. (nujol): C=0, 1660 cm"1

NMR (D6-Acetone):

complex multiplet 7.0—8.1 ppm (10H);

doublet 8.32 ppm (1H, J=4.5 Hz);

broad singlet 9.95 ppm (1H).

In a similar manner, the following compounds were prepared:

15

20

25

Example

R„

m.p., °C/oil

55

56

H

30

57

58

C1

145—8

179—81

155—8 30

169—71

8

GB 2 068 948 A 8

Example

R*

m.p., °C/oil

59

60

h ch(ch3)2

c2h5\

r c2h5

185—7

144—6

61

62

63

64

65

66

h h h ch, ch3 h

-CH,

oh och3 oh 0ch3

ch2cooc2hs ch~

140—1

oilj

171—4

oil oil

136—7

10

67

h

-chc00c2hs CH,

oil

10

68

69

70

h h h

-chc0nh2 -ch2ch20c2hs

-ch2ch2ch2och3

160—3

86—8

102—4

15

71

Compound

72

73

s-

o/Xo

158—60

m.p., °C/oil 112

107—8

128—32

15

74

n I! n

124—6

75

H \ CH,

m cha c1

169—72

9

GB 2 068 948 A 9

Compound

76

/?4 and Rs

CH:

-CH3

Br m.p., °C/oil 112

oil

77

%S

(CH3)2 CH

125—8

Other illustrative compounds of this class include:

5 Compound Name

N-[2-(5-t-butyl-1,3,4 thiadiazolyl)] 5~[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzamide 5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzoyl 2,5-dioxopyrolidine N-[2-(4,6,6-trimethyl-1,3-thiazinyl)] 5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzamide

10 N-(carboxymethyl) 5-[2-chioro-4-(trifluoromethyl)phenoxy]-2-nitrobenzamide

N-carboxymethyl-N-methyl 5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzamide N-(2,5-dichloro-3-methoxycarbonyl)phenyl 5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzamide

N-[4-[6-( 1,1 -dimethylethyl)-3-methylthio-1,2,4-triazin-5-(4H)onyl]] 5-[2-chloro-4-15 (trifluoromethyl)phenoxy]-2-nitrobenzamide

N-{3,4-dimethyl-2,6-dinitrophenyl)-N-( 1 -methylethyl) 5-[2-chloro-4-

(trifluoromethyl)phenoxy]-2-nitrobenzamide N-[2,6-dinitro-4-(trifluoromethyl)phenyl]-N-ethyl 5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzamide.

20

25

Further compounds are those in which the NR4R5 group is as follows: —NHCOOCH(CH3)2

-nhcooc2h5

—NHCOOC3H7 N (CH2CH20H)(O^

NHC(CH3)2CN NHCN

m.p. 176—9°, I.R. C=0 1760 and 1680 cm"1 m.p. 155—6°, I.R. C=0 1775 and 1692 cm"' m.p. 171—30°, I.R. C=0 1765 and 1680 cm-1

m.p. 96—8°, I.R. C=0 1635 cm"1

m.p. 63°, I.R. C=0

1655 cm"1 m.p. 100—2°, I.R. C=0 1700 cm-1 (very broad)

10

15

20

25

l/ \

"^s

/

oil I.R. C=0 1640 cm-1

/ N

\

—\ S02

oil I.R. C=0 1655 cm-1

30

— NH-

\s/

NHCH2COONa

C (CH 3 )3

207—9°, I.R. C=0 1690 cm-1

58—60° I.R. C=0 1720 and 1655 cm-1

30

10

GB 2 068 948 A 10

H. Other Benzoyl Compounds

The following 5-[2-chloro-4-(trifluoromethyl)phenoxy] 2-nitro-benzoyl compounds do not readily fall within the defined classes A—G above and are therefore listed below:

Compound 78

5 2-chloro-cyclohexyl 5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzoate (oil).

Compound 79

- -o^(OAN02 u2n—\U/— 0

[m.p. 134—6 °C]

Compound 80

S-(4-chloro-benzyl) 5-[(2-chloro-4-trifluoromethyl)phenoxy]-2-nitro-benzene carbothioate. [oil] 10 Compound 81 10

C1

F3C_(0^ u °2 °2N—'0 —^Uh-CFj

[oil]

Additional illustrative compounds are listed below:

4(2,4-difluorophenyl)-2-(methoxycarbonyl) phenyl 5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzoate

15 4-(ethoxycarbonylethyl)-2-hydroxyphenyl 5-[2-chloro-4-(trifluoromethyl)phenoxy]-2- .| 5

nitrobenzoate

3.5-dinitro-4-dipropylaminophenyl 5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzoate

2.6-bis(hydroxymethyl)-4-methylphenyl 5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-

20, nitrobenzoate 20

3-(1,2,5,6-diisopropylidene-D-glucosyl) 5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzoate 2-chloro-9-(methoxycarbonyl) 9H-fluoren-9-yl 5-[2-chloro-4-

(trifluoromethyl)phenoxy]-2-nitrobenzoate . -benzoyl(phenylmethyl) 5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzoate 25 2-(acetylamino)ethyl 5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzoate 25

2-(2-methylpropenoylamino) ethyl 5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzoate

[3-(dimethylamino)-2-methylpropionyloxy] ethyl 5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzoate

30 2-(2-methylpropenoyloxy)-2-methylethyl 5-[2-chloro-4-(trifluoromethyl)phenoxy]-2- 30

nitrobenzoate

(1-cyano-1methyl)ethoxymethyl 5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzoate

(ethoxycarbonyl) (acetyl) methyl 5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-35 nitrobenzoate 35

diethoxyphosphonylmethyl 5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzoate dimethoxyphosphinylethyl 5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzoate dimethoxyphosphinylethoxy ethyl 5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzoate 2-(chloroacetyl) ethyl 5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzoate 40 difluoromethyl 5-[2-chloro-4-(trifluorom9thyl)phenoxy]-2-nitrobenzoate 40

propenoylaminomethyl 5-[2-chloro-4-(trif!uoromethyl)phenoxy]-2-nitrobenzoate cyano(ethoxycarbonyl) methyl 5-[2-chlcro-4-(trifluoromethyl)phenoxy]-2-nitrobenzoate

4-(3-chlorophenylcarbamoyloxy)butyn-2-yl 5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzoate

45 N-(chloroacetyl)-N-(2,6-diethylphenylamino)methyl 5-(2-chloro-4-(trifluoromethyl)phenoxy]-2- 45 nitrobenzoate

3-cyanopropen-2-yl 5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzoate 5-[2-chloro-4-(trifluoromethyl)phenoxyJ-2-nitrobenzoic acid anhydride with thiocyanic acid

S-(phenylsulfonylaminoethyl) 5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-5 nitrobenzenecarbothioate

S-(2,3-dihydroxypropyl) 5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzene carbothioate S-(ethoxycarbonylmethyl) 5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-

nitrobenzenecarbothioate S-(carboxymethyi) 5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-10 nitrobenzenecarbothioate

S-[(3-fluorophenyl)methyl] 5-[2-chioro-4-(trifiuoromethyl)phenoxy]-2-nitrobenzene carbothioate

S-[(ethylthiocarbonyl) methyl] 5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzenecarbothioate 15 S-[(2,3-dihydroxypropoxycarbonyl)methyl] 5-[2-chloro-4-trifluoromethyl)phenoxy]-2-nitrobenzenecarbothioate S-[(3-ethoxycarbonyl)propen-2-yl] 5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-

nitrobenzenecarbothioate 1,1-dimethyl-2,2,2-trichloroethoxycarbonyl 5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-20 nitrobenzoate

5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzoyl O-ethylphosphonic acid ammonium salt 1 - 5-l2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrophenyl 2,2,2-trichloroethanone 1 _ 5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrophenyl 2,2,2-trifluoroethanone dimethyl 5-[2-chloro-4-trifluoromethyl)phenoxy]-2-nitrobenzoylmethylphosphonate 25 5-[2-chloro-4-(trifluoromethyl)phenoxy] 2-nitrophenyl 4-methoxy-3-methyl methanone

1- 5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrophenyl 2-(dimethoxyphosphinyl methylamino) ethanone

5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzoyl cyanade 30 N-(2,2-dimethoxyethyl) 5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzamide

N-(carboxymethyl)-N-(phosphonomethyl) 5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzamide

N-(carboxymethoxy) 5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzamide N-( 1 -methylethyl)-N-phenylmethyl) 5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-35 nitrobenzamide

3- 5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzoyl 4-chloro-2-oxobenzothiazoline N-[1,3-dihydroxy-2-methylpropyl) 5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzamide N-(diethoxyphosphinyl) 5-[2-chloro-4-(trifluoromethyl)phenoxyj-2-nitrobenzamide N-(2-sulfoethyl) 5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzamide sodium salt 40 N-(2-hexyloxysulfonyl) ethyl 5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzamide N-(trifluoroacetyl) 5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzamide N-(4-sulfophenyl) 5-[2-chloro-4-(trifluorome,thyl)phenoxy]-2-nitrobenzamide N-[(1-cyano-1-methyl)-2-ethyl] 5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzamide N-(ethoxycarbonyl) 5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzamide 45 N-[2-methyl-4-(phenylsulfonyl)phenyl] 5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzamide

N-(4-aminophenylsulfonyl)-N-(methoxycarbonyl) 5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzamide

N-[(hydroxyimino)methyl] 5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzamide 50 5-[2-chloro-4-(trifluoromethyl) phenoxy]-2-nitrobenzoic acid hydrazide

5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzoic acid methyl hydrazide 5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzoyl (2-chloroacetyl)hydrazide 5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzoyl 2-(carboxamido)hydrazide 5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzoylcyanamide 55 5-t2-chloro-4-(trifluoromethyl)-phenoxy]-2-nitrobenzoylcyanamide sodium salt 5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzoyl azide aminomethyleneamino 5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzoate 1-methylethylideneimino 5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzoate 1-(methylthio)ethylideneamino 5-[2-chloro-4-(trifluoromethyl)phenoxyJ-2-60 nitrobenzoate.

The compounds of this invention can be applied in various ways to achieve herbicidal action. They can be applied per se, as solids or in vaporized form, but are preferably applied as the toxic components in pesticidal compositions of the compound and a carrier. These compositions are

12

GB 2 068 948 A 12

>

preferably applied directly to the soil and often incorporated therewith. The compositions can be applied as granulars or dusts; as liquid sprays, or as gas-propelled sprays and can contain, in addition to a carrier, additives such as emulsifying agents, binding agents, gases compressed to the liquid state, odorants, stabilizers, and the like. A wide variety of liquid and solid carriers can be used. Non-limiting 5 examples of solid carriers include talc, bentonite, diatomaceous earth, pyrophyllite, fullers earth, gypsum, flours derived from cotton seeds and nut shells, and various natural and synthetic clays having a pH not exceeding about 9.5. Non-limiting examples of liquid carriers include water, organic solvents such as alcohols, ketones, light oils, and medium oils and vegetable oils such as cottonseed oil.

10 In practice, herbicidal application is measured in terms of pounds of herbicide applied per acre. The compounds of this invention are effective herbicides when applied in herbicidal amounts, i.e., at rates between about 0.2 and 10 kg per hectare.

The pesticidal compositions comprising the active ingredient and the carrier may be supplied either as ready-to-use compositions or as concentrates. Concentrates generally contain a higher 15 proportion of the active ingredient than the ready-to-use compositions and accordingly, require dilution prior to use. Both the ready-to-use compositions and the concentrates may be in liquid or solid form, i.e., with the active ingredient blended with a liquid or solid carrier, respectively.

The amount of active ingredient in the composition will depend, primarily, upon whether the composition is a concentrate or a ready-to-use composition. Concentrates will generally contain from 5 20 to 95% by weight, preferably 10 to 80% by weight, of the active ingredient. The concentration of active ingredient in the ready-to-use compositions will vary according to the method of application for the composition in question and to the desired application rate. In general, ready-to-use compositions will contain from 0.001 to 1, preferably 0.01 to 0.1 percent by weight of the active ingredient. Thus, the compositions may contain from 0.001 to 95% by weight of active ingredient, the actual amount 25 depending upon the nature of the composition and the method by which it shall be applied.

Concentrates may be either liquid or solid and are usually extendable with water to form emulsions or suspensions containing a smaller proportion of the active ingredient. Alternatively, liquid or solid concentrates may be extended with liquid or solid carriers to give the final ready-to-use composition. Liquid concentrates preferably comprise the active ingredient and an emulsifying agent 30 dissolved in a liquid solvent, e.g. an organic solvent of the type mentioned above. The emulsifier is suitably an anionic, cationic or non-ionic emulsifier, e.g., sodium dodecylbenzenesulfonate or an ethylene oxide derivative of an alkyl phenol, a mercaptan, an amine or a carboxylic acid. Liquid concentrates may advantageously contain from 10 to 30 weight percent e.g. 25 weight percent of the active ingredient e.g. 1 kg of active ingredient per 4 kg of concentrate.

35 Wettable powders are another preferred form of concentrate and these suitably comprise the active ingredient, a finely-divided solid carrier and at least one surfactant to impart wettability or dispersability. Solid carriers which are suitable for preparing wettable powder formulations may be either organic or inorganic in nature. Suitable organic carriers are soybean, walnut, or wood flour or tobacco dust, and suitable inorganic ones are clays of the bentonite, kaolinite, of fuller's earth types; 40 silicas such as diatomaceous earth, silicates such as talc, pyrophyllite, or alkaline earth silicates, and calcium and magnesium carbonates. The carrier may be a single substance or a mixture of finely divided solids. A surfactant or mixture of surfactants is generally present in an amount of 1 to 10 • percent by weight of the wettable powder formulation. Suitable dispersing agents are sodium formaldehydenaphthalene sulfonate or sodium lignin sulfonate. Wetting agents include higher alkylaryl 45 sulfonates ("higher alkyl" meaning alkyl of at least 8 carbon atoms) such as calcium dodecylbenzenesulfonate, alcohol sulfates, alkylphenoxyethoxyethoxyethyl sodium sulfonates, sodium dioctyl sulfosuccinate, and ethylene oxide adducts with fatty alcohols, fatty acids, or with higher alkyl-phenols, such as octylphenoxypolyethoxyethanol. Sticking or spreading agents may be included such as glycerol mannitan laurate or a condensate of polyglycerol and oleic acid modified with phthalic 50 anhydride. The active ingredient content of the wettable powder may be in the range of 20 to 80% by weight; however, the preferred range of concentrations is 50% to 80%.

Dusts may be made by incorporating the active ingredient into a solid carrier, such as finely powdered clays, talc, silica, and synthetic silicates, alkaline earth carbonates, and diluents of natural origin such as tobacco dust or walnut shell flour. Granular formulations can be made from similar type 55 solid carriers except that the particle size is larger in the range of 15 to 60 mesh (U.S. Standard Sieve Series). A small amount of dispersing agent may be incorporated in these solid formulations. The concentration of active ingredients in these dust or granular formulations may be in the range of 1 to 20% by weight. The solid carriers used in these formulations may be essentially inert or they may consist wholly or in part of fertilizing materials such as ammonium sulfate, or other ammonium salts, 60 urea, calcium phosphates, potassium chloride or dried blood.

One particularly convenient method for making solid formulations is to treat the solid carrier with the active ingredients dissolved in a solvent and allow the solvent to evaporate off. This results in the carrier which is usually in the form of finely divided particles, being impregnated with the active ingredients. Another method is to apply the mixture of active ingredients in the molten state or by 65 spraying.

5

10

15

*

20

25

30

35

40

45

50

55

60

65

13

GB 2 068 948 A 13

The concentration of the active ingredient in the final ready-to-use composition will depend not only upon the application rate desired (generally in the range of 0.2 to 10 kg per hectare, as mentioned above), but also upon the application method which is to be used. Wettable powders and liquid concentrates are usually applied as aqueous sprays and applied at application rates varying from about 5 10 to 1500 liters per hectare. With ground equipment, the application rate will generally be in the 5

range of 100 to 500 liters per hectare, whereas aerial spray equipment will generally apply 15 to 80 liters per hectare.

Herbicidal Effectiveness

Method of Propagating Test Species

10 Crop and weed species are planted in 8"x10" disposable fiber flats containing potting soil to 10 provide each flat with a 4" row of all test species. Crop species consists of field corn (CN), crabgrass (CG), cotton (CT), and soybeans (SB). The weed species consist of foxtail millet (FM), green foxtail (GF), velvetleaf (VL), cocklebur (CB), wild mustard (WM) and pigweed (PW).

; Cotton, corn, soybean, and cocklebur plantings consist of 4 to 5 seeds per row depending upon

15 species. The smaller seeded species (velvetleaf, wild mustard, pigweed, foxtail millet and green foxtail) 15 are planted in an uncounted but sufficient number to provide a solid row of seedlings.

Plantings for the pre- and post-emergence portions of the test are identical as to seeding. The initial watering until emergence is done from the top. The post-emergence phase is propagated in advance so as to provide plants of the proper stage of development at the time of treatment. Plantings

20 for the pre-emergence phase are made not more than one day in advance of treatment. 20

The desired stage of development for treatment of the post-emergence broadleaf species (CT, SB, CB, VL, WM, PW) is the one true leaf or first trifoliate leaf stage. The desired stage for corn would be a height of 3—4", while a 2" height would be adequate for the grasses.

Method of Treatment

25 Spray applications are made with a handgun sprayer (aspirator type) simultaneously to one flat of 25 established plants for the post-emergence phase and one newly seeded flat for the pre-emergence phase. The 10 lb/acre treatment rate consists of the uniform application of 116 milligrams of test compound to the combined area of the two flats (160 sq. inches). Application is made in a solvent mixture consisting of 40 ml acetone and 40 ml water and a surfactant concentration of 0.1 %.

30 Following spray application, flats are returned to the greenhouse where watering of the post- 30 emergence phase is done only by subirrigation. The pre-emergence phase is top watered by sprinkling until after test species have emerged. Subsequent watering is by subirrigation.

Two weeks after treatment, the pre- and post-emergence injury and control is rated on a 0— 100% injury and control scale. Special physiological effects are rated as to intensity also at this time.

35 The herbicidal test data reported for compounds 1—81 was obtained at application rates of 10 35 lbs down to 1/4 lb/acre. The following lists the metric equivalents for each rate.

Application Rate

Us—lb/acre Metric—kg/ha 10.0 11.2

40 4.0 4.48 40

2.0 2.24

1.0 1.12

0.5 0.56

0.25 0.28

45 Test results are set forth in Table I (pre-emergence and Table II (post-emergence). 45

Table I

Dosage Pre-Emergence Cpd. Lbs) — ——

No.

Acre

CG

FM

GF

VL

CB

WM

PW

CT

CN

SB

50

1

10

100

90

0

100

10

0

4

100

90

20

—

100

—

0

2

100

60

10

—

100

70

0

10

1

90

30

0

100

20

0

10

1/2

90

80

0

90

100

20

0

10

55

1/4

90

70

30

0

90

80

0

10

0

0 50

55

14

5

10

15

20

25

30

35

40

45

50

GB 2 068 948 A 14

Table I (Continued)

Dosage Pre-Emergence

Cpd. Lbs/

No. Acre CG FM GF VL CB WM PW CT CN SB

2 10 — 20 20 10 0 70 90 0 0 0 5

4 __________

2 __________

1 __________

1/2 __________

1/4 — — — — — — — — — — 10

3 10

4

2 1

1/2 15

1/4

10 4 2

11 10

4

12

—

90

0

90

100

0

—

100

90

30

20

90

100

10

0

60

10

0

10

30

80

0

100

90

20

100

10

0

10

—

100

90

0

—

100

—

0

10

90

40

0

70

60

0

90

70

30

100

60

0

—

90

10

40

100

20

0

10

""

70

10

0

70

100

0

10

100

90

70

20

100

0

40

0

—

100

90

10

0

100

40

0

—

90

60

0

40

90

30

0

—

70

80

10

0

50

90

10

0

10

—

20

0

10

30

0

20

10

0

100

40

0

70

20

0

70

0

—

0

30

0

—

0

—

10

60

10

0

—

10

0

50

60

0

—

10

0

10

—

0

10 4 2

1 __________ 20

1/2 1/4

4

2

1 — 70 10 0 0 70 100 0 0 10 25 1/2 1/4

4

2

1

1/2 1/4

4

2

1 __________ 35

1/2 1/4

10 4

2 __________ 40

4 2 1

1/2

1/4 __________ 45

4

—

100

90

60

100

40

10

0

2

—

100

90

40

10

100

10

30

0

1

—

100

90

0

100

0

1/2

—

70

30

10

0

90

30

0

1/4

—

20

0

20

60

30

15

GB 2 068 948 A 15

Table I (Continued)

Cpd. No.

Dosage Lbs/ Acre

Pre-Emergence

CG

FM

GF

VL

CB

WM

PW

CT

CN

SB

5

13

10

90

100

80

100

90

10

5

4

90

70

10

90

10

20

0

2

—

90

70

30

0

90

0

1

1/2

_

10

1/4

—

■

14

4

—

70

50

10

0

70

60

0

20

0

1

1/2

—

•

1/4

'

15

4

_

100

90

40

20

90

10

0

15

2

90

10

0

90

0

1

70

60

10

0

20

80

20

0

10

1/2

1/4

20

16

4

90

50

10

0

90

70

10

0

20

2

80

10

0

70

0

10

1

1/2

1/4

25

17

4

_

100

90

40

0

100

0

10

0

25

2

—

90

30

0

90

30

0

10

1

1/2

1/4

30

18

10

_

100

80

70

0

100

10

0

30

2

100

40

20

10

100

10

0

10

1/2

—

90

20

0

10

100

90

10

30

1/4

—

10

40

10

80

60

10

0

19

10

100

80

60

100

30

60

0

35

2

100

70

40

10

100

20

10

35

1/2

100

60

0

100

60

10

0

1/4

—

10

60

20

70

50

20

0

20

4

90

80

50

0

100

90

0

2

80

20

10

20

90

20

0

10

40

1

0

20

30

10

40

-

1/2

1/4

-•

21

4

80

60

20

0

30

20

10

20

2

—

45

22

4

90

80

20

0

90

0

10

0

45

2

80

70

20

0

80

60

0

20

0

1

—

90

20

10

20

30

10

40

10

50

1/4

—

23

4

80

0

10

0

90

30

10

0

50

2

—

70

10

30

0

70

10

0

50

1/2

1/4

25

26

27

28

29

30

31

32

33

34

36

37

38

39

GB 2 068 948 A 16

Table I (Continued)

Dosage

Pre-Emergence

/ /ic/

LUo/

Acre cg

FM

GF

VL

CB

WM

PW

CT

CN

SB

4

90

70

60

10

90

0

10

5

2

80

70

40

0

70

80

0

Ml

■

0

10

0

10

0

1/4

4

100

90

20

100

10

40

10

2

90

80

40

100

40

10

20

10

1

100

90

10

0

90

0

-

1/2

90

70

0

90

70

10

0

10

1/4

10

20

10

0

20

0

2

___

40

20

70

90

70

0

10

*

1/2

10

0

10

0

90

40

0

15

1/4

2

_

90

80

0

100

10

0

1/2

70

50

40

0

90

100

0

1/4

50

10

0

70

10

0

2

90

20

100

50

10

20

1/2

90

20

0

100

10

0

1/4

60

20

0

—

50

80

10

0

2

100

40

10

100

0

20

1/2

100

90

0

100

90

10

0

1/4

10

40

60

0

90

0

25

1/2

10

60

30

—

90

____

1/4

10

40

10

—

10

—

2

60

50

10

0

80

90

30

20

0

1/2

—

10

0

19

0

10

50

0

1/4

—

30

2

90

70

0

100

10

0

10

1/2

—

90

0

90

80

0

10

1/4

—

30

10

0

10

0

2

100

90

50

0

90

10

40

1/2

—

80

10

0

20

10

0

35

1/4

2

100

10

30

90

30

10

0

1/2

—

20

10

80

20

0

1/4

2

50

20

40

20

90

10

20

30

40

1/2

—

0

—

20

50

10

1/4

2

60

0

80

20

0

1/2

—

0

—

0

1/4

45

2

100

90

50

10

100

60

0

1/2

—

90

50

0

50

40

0

1/4

2

90

70

20

100

10

20

0

50

1/2

—

90

70

10

100

0

17

GB 2 068 948 A 17

Dosage

Table I (Continued)

Pre-Emergence

Cpd. No.

Lbs/ Acre

CG

FM

GF

VL

CB

WM

PW

CT

CN

SB

40

2

100

90

0

100

10

0

5

1/2

—

90

70

20

0

100

90

10

0

41

2

_

100

90

40

0

100

90

10

0

1/2

—

90

30

0

90

70

0

1/4

—

0

10

0

42

2

100

90

70

100

90

20

30

10

Ml

100

80

60

100

90

20

30

1/4

—

80

90

10

0

60

90

10

0

10

43

1/2

90

50

0

90

100

—

1/4

60

90

50

—

10

—

44

2

100

90

30

100

60

20

30

15

1/2

90

80

10

100

20

10

20

1/4

20

0

90

20

0

10

45

2

_

100

70

10

100

10

0

1/2

90

80

10

0

100

0

1/4

90

10

0

80

90

0

20

46

2

_

100

90

20

10

100

90

10

0

1/2

90

10

30

90

70

10

0

1/4

30

20

0

47

2

100

90

20

100

30

10

0

25

1/2

100

90

20

10

100

10

0

1/4

20

0

90

20

10

0

48

2

100

70

100

0

1/2

100

90

30

0

90

60

40

0

49

2

90

60

0

90

100

0

1/2

20

0

10

100

90

0

10

30

50

2

90

50

100

50

10

30

1

90

20

0

100

90

0

1/2

80

70

10

0

100

90

10

20

1/4

90

70

20

10

90

80

0

51

10

100

50

100

10

30

0

35

4

___

100

90

60

100

20

10

20

2

—

90

70

10

100

20

0

10

1

___

100

10

0

100

0

10

1/2

90

50

0

10

70

40

0

40

1/4

—

'

_

52

10

100

90

100

—

1

60

70

60

0

90

—

1/2

40

80

50

10

80

—

1/4

53

10

90

50

100

50

10

0

45

4

90

30

—

100

10

0

1

90

60

0

—

90

0

1/2

10

0

10

—

20

90

0

1/4

—

.10

15

20

25

30

35

40

45

54

55

56

57

58

59

60

61

62

63

64

65

66

GB 2 068 948 A 18

Table 1 (Continued)

Dosage Pre-Emergence

LOS/

Acre

CG

FM

GF

VL

CB

WM

PW

CT

CN

SB

4

0

5

2 1

1/2

1/4

4

0

20

40

10

90

100

60

0

20

10

2

0

I

1/2

1/4

4

0

30

70

100

30

0

15

2

4

10

0

70

90

0

2 1

1/2

20

1/4

4

30

0

10

100

0

2 1

10

0

100

0

25

10

0

10

0

10

70

0

4

2

50

20

60

10

90

80

20

10

20

1/2

0

50

0

1/4

30

4

90

100

80

100

1

90

40

70

—

100

—

1/2

40

0

10

0

80

—

4

90

100

1

60

40

70

—

90

0

—

35

1/2

20

0

20

0

10

0

—

4

90

100

2

90

50

—

100

90

—

1

20

0

40

0

90

0

—

1/2

0

20

0

70

—

40

4

80

90

100

2

—

30

70

20

0

80

100

0

1

—

90

70

80

0

90

10

0

1/2

—

10

50

0

100

0

1/4

—

30

10

0

70

80

0

45

4

90

100

1

70

40

—

70

—

100

—

1/2

0

10

—

20

0

60

0

—

19

GB 2 068 948 A 19

Table I (Continued)

Dosage

Pre-Emergence

/ /)c/

KsfJU.

L.Uof

No.

Acre

CG

FM

GF

VL

CB

WM

PW

CT

CN

SB

5

67

4

90

—

100

—

2

60

70

—

60

—

90

—

1

0

—

10

0

40

0

—

1/2

0

—

40

10

90

20

—

111

68

10

100

90

100

—

100

—

0

10

4

100

90

60

100

0

10

2

90

10

100

20

1

90

30

90

0

100

40

0

1/2

70

80

70

50

100

10

0

1/4

—

80

60

0

100

20

0

15

69

2

100

90

60

50

100

10

40

20

1/2

100

90

10

100

0

10

1/4

—

0

60

10

80

10

50

10

70

2

100

90

50

100

10

20

1/2

—

100

90

10

30

100

20

0

10

20

1/4

—

0

10

50

0

90

0

40

80

71

2

90

50

40

0

90

80

10

1/2

—

10

0

10

90

10

0

10

1/4

—

1

72

10

90

20

90

40

70

25

2

—

90

70

0

100

10

20

0

1

90

80

0

90

80

10

0

1/2

20

0

10

—

90

20

10

1/4

—

30

0

10

—

70

80

0

20

10

73

10

100

90

30

100

20

60

0

30

4

100

90

80

60

100

90

50

70

10

2

80

70

10

100

10

0

1

90

60

10

0

90

60

20

0

10

1/2

—

90

50

0

90

80

0

74

2

90

70

0

100

10

0

35

1/2

90

70

0

90

50

10

0

1/4

—

0

10

0

70

10

0

10

75

2

•i

—

60

20

0

50

80

0

1

1/2

—

40

1/4

76

2

80

40

80

0

70

20

60

10

1/2

—

10

0

70

10

0

1/4

—

77

2

100

90

10

0

100

90

0

45

1/2

—

90

70

0

10

90

60

10

0

78

10

90

100

—

100

—

4

90

0

100

0

2

90

80

0

90

100

10

0

1

40

60

10

100

0

50

1/2

50

70

0

—

90

0

1/4

—

80

50

20

0

90

60

10

30

0

10

15

20

25

30

35

45

50

20

GB 2 068 948 A 20

Table I (Continued)

Cpd. No.

Dosage Lbs/ Acre

Pre-Emergence

CG

FM

GF

VL

CB

WM

PW

CT

CN

SB

5

79

10 1/4

70 0

90 0

—

50 0

—

90 0

—

5

10

80

4 2 1

1/2 1/4

—

100 90 10

90 80 0

40 10 0

20 10 0

90 90 70

90 10 20

0 10 0

20 10 0

10 10 0

10

81

2 1/2 1/4

—

80 10

50 0

0 0

90 10

80 60

0 0

,

15

Cpd. No.

Dosage Lbs/ Acre

Table II

Post-Emergence

15

CG

FM

GF

VL

CB

WM

PW

CT

CN

SB

20

25

30

35

40

45

50

10

—

100

80

60

4

—

90

100

90

60

50

20

2

—

100

—

100

—

90

50

20

1

—

100

90

100

—

100

90

30

50

1/2

—

100

90

100

80

70

10

1/4

—

50

40

80

100

60

50

40

10

90

80

90

100

90

10

25

4

—

100

90

60

90

10

2

—

90

80

100

90

20

1

—

90

80

90

100

90

70

1/2

—

80

70

60

90

100

90

80

30

1/4

—

90

70

80

100

80

90

50

60

30

10

90

100

30

4

—

100

90

100

90

30

10

2

—

100

90

100

90

100

90

20

1

—

90

100

80

70

60

1/2

—

90

100

90

60

35

1/4

—

90

80

90

80

100

90

30

10

100

90

50

4

—

100

—

100

—

100

90

30

2

—

90

100

20

1

—

100

—

100

40

50

40

1/2

—

100

90

100

70

10

1/4

—

50

70

30

50

90

100

40

30

50

4

100

90

100

90

0

40

2

—

90

100

—

100

—

90

10

20

1

—

90

100

0

100

90

50

10

45

1/2

—

80

70

90

80

100

90

20

1/4

—

60

50

70

90

100

60

30

60

4

100

10

60

2

—

100

90

80

40

1

—

70

80

70

100

60

70

60

50

1/2

—

90

100

90

80

20

1/4

—

80

60

80

50

90

70

90

10

j

5

10

15

20

25

30

35

40

45

50

J21

5

10

15

20

25

30

35

40

45

50

GB 2 068 948 A

Table II (Continued)

Dosage Post-Emergence

Cpd. No.

Lbs/ Acre

CG

FM

GF

VL

CB

WM

PW

CT

CN

SB

1

4

100

80

100

80

100

80

0

20

2

90

30

100

—

90

100

90

10

20

1

90

70

100

—

90

100

90

—

40

1/2

90

100

—

90

100

90

10

50

1/4

90

50

100

60

30

40

8

10

90

80

100

60

90

100

40

0

20

4

60

30

—

70

—

70

20

0

2

80

70

50

—

70

90

0

10

9

4

90

100

40

90

100

90

10

20

2

90

—

90

100

90

10

30

1

90

100

80

100

90

0

10

1/2

100

90

70

100

80

10

1/4

70

80

30

50

90

100

50

40

10

4

80

20

70

10

90

50

90

40

10

2

50

70

0

90

70

90

70

30

11

10

90

70

30

80

100

40

0

10

4

30

20

30

20

70

90

80

30

10

12

4

90

100

90

100

90

20

10

2

100

90

100

70

40

1

100

60

10

1/2

100

90

80

100

80

60

1/4

90

70

100

90

60

50

13

10

90

100

90

80

20

4

100

90

2

100

90

100

90

50

1

90

70

100

90

70

50

1/2

90

80

70

100

90

70

60

1/4

90

80

100

90

60

14

4

90

80

100

90

30

20

1

90

80

10

90

70

40

1/2

90

70

90

80

70

20

1/4

80

70

50

90

100

80

50

70

15

4

90

100

90

100

60

10

2

90

100

90

70

30

1

90

80

60

90

100

90

50

30

1/2

90

100

90

50

30

1/4

90

70

60

50

70

90

70

50

70

16

4

90

60

50

100

90

50

10

2

30

40

60

30

90

80

70

50

80

1

70

60

70

90

60

70

1/2

90

70

80

100

90

60

40

1/4

60

40

60

30

90

100

60

50

17

4

100

90

100

90

70

30

2

100

90

100

80

40

1

90

80

60

90

100

70

40

1/2

90

70

10

1/4

80

50

90

60

90

40

10

22

GB 2 068 948 A 22

Table II (Continued)

Dosage Post-Emergence Cpd. Lbs/

No.

Acre

CG

FM

GF

VL

CB

WM

PW

CT

CN

SB

5

18

10

—

100

90

100

90

5

2

—

90

100

90

100

90

80

1/2

—

90

100

70

100

80

70

60

1/4

—

90

70

90

50

100

70

50

19

10

—

100

90

100

90

80

40

10

2

—

90

100

90

60

40

10

1/2

—

90

100

90

80

40

1/4

—

90

70

40

100

50

60

20

4

90

80

100

90

40

20

2

—

70

80

90

70

90

60

40

15

1

—

80

60

70

90

80

90

50

20

15

1/2

—

20

60

30

90

30

1/4

—

50

40

100

50

40

50

21

4

—

80

70

90

40

90

50

20

2

—

10

20

70

80

70

30

20

22

4

.—

90

70

90

100

90

80

30

20

2

—

80

90

20

90

100

90

80

50

1

—

90

70

40

90

—

60

50

70

1/4

—

50

60

10

80

50

10

25

23

4

90

80

60

90

100

90

80

2

—

90

70

90

—

90

40

25

1/2

—

20

10

90

80

10

1/4

—

70

30

20

80

70

80

10

30

24

4

100

90

100

90

2

—

100

80

100

—

90

50

70

30

1/2

—

60

50

70

20

80

100

90

20

30

1/4

—

70

80

70

50

90

10

40

25

4

9

—

100

90

80

1

100

90

100

90

100

90

70

35

1/2

—

90

100

90

35

1/4

—

80

90

80

90

40

30

26

2

50

70

100

90

100

90

30

60

1/2

—

10

0

90

50

90

50

20

40

1/4

—

20

10

60

80

90

100

50

10

50

40

27

2

100

90

70

90

40

1/2

—

100

90

100

90

60

1/4

—

70

60

90

70

100

60

90

50

80

28

2

100

90

100

90

45

1/2

—

90

100

90

60

1/4

—

90

80

100

70

80

45

29

2

100

90

100

60

90

1/2

—

90

100

80

100

90

10

80

1/4

—

90

100

70

100

90

50

80

50

30

1/2

20

100

90

80

60

1/4

90

70

100

90

20

40

50

23

GB 2 068 948 A 23

Table II (Continued)

Dosage Post-Emergence Cpd. Lbs/ ———

No.

Acre

CG

FM

GF

VL

CB

WM

PW

CT

CN

SB

5

31

2

90

100

90

100

90

30

60

5

1/2

—

90

100

70

90

100

90

60

30

1/4

—

80

100

60

80

100

80

30

70

32

2

100

90

100

40

80

1/2

—

100

80

100

20

80

10

1/4

—

30

20

100

90

70

60

40

10

•

33

2

100

90

100

70

80

1/2

90

100

70

100

70

80

«

1/4

—

80

70

90

100

70

10

40

34

2

70

100

90

100

90

60

15

1/2

—

60

100

90

100

80

40

15

1/4

—

90

70

90

100

50

20

50

36

2

100

90

80

100

90

50

1/2

—

90

30

90

100

90

70

60

1/4

—

20

30

90

—

90

40

10

20

37

2

90

80

0

90

80

70

20

1/2

—

90

—

90

40

1/4

—

10

70

—

80

70

50

10

30

38

2

90

100

90

100

90

50

60

1/2

90

100

90

100

60

10

50

25

1/4

—

30

20

90

80

100

70

10

25

39

2

90

100

60

90

1/2

—

90

100

40

70

40

2

100

90

1/2

—

90

100

90

100

30

70

30

41

2

100

90

30

1/2

—

90

100

90

100

90

30

80

1/4

—

70

80

90

70

100

90

20

60

42

2

100

90

1/2

100

90

100

90

35

1/4

—

100

80

100

90

50

80

35

43

1/2

70

100

90

100

40

•

1/4

100

—

90

100

70

40

30

44

2

100

90

1/2

100

90

100

90

80

40

1/4

—

90

70

100

90

60

40

45

2

100

90

1/2

100

90

100

80

60

1/4

—

100

90

100

90

50

60

46

2

100

90

100

90

45

1/2

100

70

90

100

70

50

45

1/4

—

90

30

90

50

47

2

100

90

80

1/2

—

90

70

90

100

90

50

30

1/4

—

90

60

20

100

80

20

60

48

49

50

51

52

53

54

55

56

57

58

59

60

GB 2 068 948 A 24

Table II (Continued)

Dosage Post-Emergence

Lbs/ —

Acre CG FM GF VL CB WM PW CT CN SB

2

—

100

90

1/2

—

90

2

50

10

90

70

1/2

—

10

20

70

30

2

—

90

60

90

1

—

90

100

1/2

—

60

80

90

70

1/4

—

90

80

90

70

10

100

80

4

—

100

2

—

90

100

90

1

—

100

1/2

—

60

80

100

80

1/4

—

100

90

100

70

10

70

90

100

1

70

40

—

100

50

1/2

30

20

—

70

20

1/4

20

90

—

30

20

10

100

90

4

100

90

—

80

1

90

—

70

60

1/2

40

—

20

0

1/4

20

10

—

10

—

4

30

80

30

2

—

20

10

—

1

—

80

90

40

1/2

—

60

50

10

—

1/4

—

20

40

30

50

4

20

10

20

2

—

30

0

—

1

—

80

20

30

1/2

—

80

10

—

1/4

—

20

30

0

30

4

80

90

50

70

2

—

30

10

30

—

4

60

80

40

30

2

—

70

40

0

—

1

—

60

50

0

—

1/2

—

20

30

20

—

1/4

—

20

10

30

4

40

70

0

40

2

—

10

0

—

1

—

50

30

20

10

—

0

10

0

10

80

60

10

70

4

—

20

10

20

100

90

80

5

100

40

90

100

60

20

30

100

90

40

30

100

90

70

40

100

80

90

60

1-0

100

80

0

10

100

40

0

30

100

90

70

100

90

70

100

90

70

40

15

100

80

90

80

100

90

10

20

100

90

50

0

40

100

80

30

100

80

10

40

20

90

100

40

10

100

70

30

10

100

90

100

70

80

100

90

60

50

25

100

90

80

20

50

90

50

20

10

30

100

40

10

90

20

10

90

50

10

20

30

90

30

10

80

60

40

10

100

0

10

100

80

20

0

80

90

100

30

20

30

35

90

—

80

0

10

30

0

10

100

20

10

60

80

70

0

10

90

100

70

0

10

40

100

60

10

90

60

40

30

s

90

100

50

10

20

60

80

50

10

90

100

30

20

45

90

100

10

0

10

70

100

30

20

30

0

80

0

90

100

30

10

80

70

50

0

10

50

25

GB 2 068 948 A 25

Table II (Continued)

Dosage

Post-Emergence

/■>_ J

/ A « /

Q*pd.

Lbs/

CT

CN

SB

No.

Acre

CG

FM

GF

VL

CB

WM

PW

61

2

_

30

20

90

60

100

80

30

1/2

20

30

80

50

100

70

20

30

1/4

60

90

70

90

100

40

20

30

62

4

20

_

0

20

100

30

10

20

1

0

10

60

70

30

0

30

1/2

30

0

10

70

50

10

0

20

63

4

0

90

20

30

1

0

30

20

10

50

80

10

20

1/2

20

0

70

60

10

0

30

64

4

0

20

_

10

30

100

60

10

2

0

10

20

10

100

90

70

10

1

20

10

20

80

50

20

0

10

1/2

10

80

60

0

10

20

65

4

10

20

—

30

100

70

20

40

2

70

90

100

90

100

90

20

10

1

90

100

90

100

80

30

40

1/2

—

90

—

90

100

20

10

1/4

—

50

40

70

90

100

80

30

40

66

4

0

40

_

10

20

90

100

20

40

30

1

0

10

50

60

50

70

0

40

1/2

10

20

40

50

10

0

40

67

4

20

__

10

60

40

100

50

40

50

2

10

30

50

100

80

10

20

1

20

0

10

20

100

20

10

40

1/2

20

0

10

40

30

100

10

20

68

10

20

30

100

90

20

50

4

100

90

60

2

100

90

100

80

60

90

1

30

50

100

—

90

100

90

20

30

1/2

90

100

—

90

100

90

70

90

1/4

50

40

80

90

100

70

30

60

69

2

100

90

100

80

100

90

80

70

1/2

90

100

70

90

70

40

70

1/4

50

40

100

60

90

50

60

70

2

_

90

80

100

70

100

90

70

60

1/2

90

80

100

60

100

90

20

50

1/4

90

70

100

50

90

80

20

40

71

2

40

60

100

90

100

90

20

60

1/2

40

100

90

100

90

10

50

1/4

20

10

60

80

90

100

50

10

50

72

10

100

90

80

2

100

90

100

80

1

100

90

100

80

1/2

90

100

90

50

80

1/4

90

80

100

30

80

10

15

20

25

30

35

40

45

10

15

20

25

30

35

40

45

26

GB 2 068 948 A 26

Table II (Continued)

Dosage

Post-Emergence

Cpd.

Lbs/

No.

Acre

CG

FM

GF

VL

CB

WM

PW

CT

CN

SB

5

73

10

100

70

100

90

80

50

4

90

100

90

100

90

70

40

2

30

50

70

40

100

50

10

30

1

40

50

70

90

100

50

20

30

1/2

90

80

70

100

70

20

10

74

2

90

80

90

10

100

90

10

40

1/2

90

80

90

—

100

90

20

30

1/4

60

80

90

10

40

75

2

80

70

60

20

90

100

90

10

20

1

90

80

40

100

70

20

15

1/2

20

50

10

90

10

1/4

10

70

—

60

20

50

0

20

76

2

20

10

40

90

100

90

10

50

1/2

10

90

60

10

40

1/4

10

80

30

80

70

40

10

20

77

2

90

100

90

100

50

20

30

1/2

90

80

100

30

10

30

78

10

60

20

70

100

90

70

30

4

—

80

90

100

90

100

90

0

10

2

—

100

90

100

90

50

70

25

1

—

90

100

60

100

40

80

40

1/2

—

90

80

90

—

30

20

1/4

—

40

80

40

50

80

100

40

79

10

50

60

80

100

80

10

20

1/4

70

80

40

80

90

100

70

10

30

80

4

90

100

50

100

90

30

2

—

70

50

90

50

90

60

90

60

90

1

—

70

80

20

90

40

10

1/2

—

30

70

50

90

60

20

1/4

—

50

40

50

80

100

50

20

50

35

81

2

40

90

70

100

90

30

60

1/2

—

30

100

50

100

90

10

40

1/4

—

40

90

30

90

50

10

30

Claims

1.

Herbicidal compounds of the formula

0

II

Xn

/ -

-C1

\

II

c -

/

40

CF3-

-<0

0 -

O V

no2

/ Q

/x£/

r

10

15

20

25

30

35

40

where Q is 0 or S, n is an integer from 1 to 5, and X is selected from N02; lower alkyl of C.,_4; halogen; phenyl; COOR where R is lower alkyl of C.,_4, H or a cation selected from alkali metals, alkaline earth metals, ammonium and lower alkyl and di-lower alkyl ammonium; CN; lower alkyl thio of C1-4; lower alkoxy of C,_4; trifluoromethyl; and combinations thereof.

45

2. The compounds of Claim 1 wherein n is an integer from 1 to 3.

3. The compounds of Claim 2 wherein Q is 0.

4. The compounds of Claim 3 wherein X is selected from the group consisting of N02, halogen, CN, COOR and CF3 and combinations thereof.

5. Herbicidal compounds of the formula

45

27

GB 2 068 948 A

27

CF

6. The compounds of Claim 5 wherein Q is 0.

7. The compounds of Claim 5 wherein Het is pyridine or substituted pyridine.

8. Herbicidal compounds of the formula

0

CI

CF:

O

C-O-subst. alkyl \ - 4 (j)—N02

wherein the substituents on the straight or branched C1-4 alkyl group are selected from cyano; phenyl;

Xn where n is 1 to 5 and X is selected from N02, lower alkyl of C,^, halogen, phenyl, phenoxy, CN, lower alkyl thio of C^, lower alkoxy of C,^,, trifluoromethyl and combinations thereof;

0 0

II II

—C—R2; —0—C—R2

phenoxy; nitro; SR,; SOR,; SC^R,;

15 where R, is an alkyl of 1 to 3 carbons and R2 is an alkyl or alkenyl of up to 3 carbons and wherein one or more of said substituents can be attached to any one or more of the carbons on said straight or branched C,_4 alkyl group.

9. The compounds of Claim 8 wherein the substituents on the alkyl group are selected from the group consisting of cyano,

10

15

20

0

II

—C—CH3, SCHg, SOCH3, S02CH3. 10. Herbicidal compounds of the formula

20

CF

where Q is 0 or S and Y is a straight or branched alkoxy, alkylthio, alkenyloxy or alkenylthio of 1 to 6 carbons, a dialkylamino of 2 to 6 carbons, or a heterocyclic amine such as morpholine. 25

11. The compounds of Claim 10 wherein Y is a straight or branched alkoxy or alkylthio of 1 to 6 carbons.

12. Herbicidal compounds of the formula

25

C — P— (OR 3 ) 2

wherein R3 is straight or branched alkyl of 1 to 6 carbons.

28

GB 2 068 948 A 28

10

15

20

25

30

13. The compounds of Claim 12 wherein R3 is a straight or branched alkyl of 1 to 3 carbons.

14. Herbicidal compounds of the formula where A is an alkyl of 1 to 3 carbons or hydrogen.

15. The compounds of Claim 14 wherein A is hydrogen or methyl.

16. Herbicidal compounds of the formula wherein R4 is selected from hydrogen and straight or branched chain alkyl of 1—4 carbon; Rs is selected from: phenyl;

10

where n is 1 to 5 and X is selected from N02, lower alkyl of C,^, halogen, phenyl, COOR where R is lower alkyl of C,^ or H or a cation, CN, lower alkyl thio of C1-4, lower alkoxy of C,_4, trifluoromethyl and combinations thereof; heterocyclicalkyl and heterocyclic, said heterocyclics of a 5 to 7 member ring comprising carbon in combination with one or more of sulfur, oxygen and nitrogen; hydroxy!, alkoxy of 1—3 carbons; —R6C02Re, where Re is an alkyl or alkenyl of up to 3 carbons; —R6C0NH2; R6C0NHR2 or R6C0N(R2)2; alkoxyalkyl where the alkoxy and alkyl may each contain a straight or branched C,_3 alkyl chain; or where R4 and Rs together form a heterocyclic ring as hereinabove defined.

15

17. The compounds of Claim 16 wherein R5 is wherein n is an integer of 1 to 3 and X is selected from the group consisting of N02, COOR and cyano and combinations thereof.

18. The compounds of Claim 16 wherein the heterocyclics for Rr are selected from the group consisting of pyridine, tetrahydrofuran, thiophene.

19. The compounds of Claim 16 wherein R5 is selected from the group consisting of alkoxy of 1 — 3 carbons, alkoxyalkyl where the alkoxy and alkyl moieties may each contain one to three carbons, and ReC0NH2.

20. The compounds of Claim 16 wherein R4 and R5 together form a heterocyclic ring selected from the group consisting of five and six member rings comprising carbon in combinations with one or more of sulfur, oxygen and nitrogen and wherein said heterocyclic ring can be substituted by one or more substituents selected from halogen, methyl and nitro and wherein said heterocyclic ring can be part of a bicyclic group, said second ring being phenyl.

21.

20

25

30

01

F3C

22.

c1

35

F3C

O

Oh-CF:

35

29

GB 2 068 948 A 29

23.

24.

¥

f3c

CI

cs no2

CF-,

25. A herbicidal composition comprising a compound of any one of Claims 1 to 24 and a carrier therefor.

26. A method for combating undesirable herbs which comprises contacting them with a herbicidally effective amount of a compound according to any one of Claims 1 to 24.

Printed for Her Majesty's Stationery Office by the Courier Press, Leamington Spa, 1981. Published by the Patent Office, 25 Southampton Buildings, London, WC2A 1 AY, from which copies may be obtained.