2-Nitro-5(substituted-phenoxy) benzoyl derivatives as herbicides

Abstract

There is provided a new class of derivatives of 2-nitro-5-(substituted-phenoxy) benzoyl compounds that have pre- and post-emergence herbicidal activity. The derivatives include certain substituted phenyl esters, phenyl thioesters; heterocyclic esters; substituted alkyl and alkylthio esters; carbonates and thiocarbonates; benzoyl phosphonates; substituted alkanones and substituted amides.

Description

Applicant Theissen herein has been granted a series of patents relating to 2-nitro-5-(substituted-phenoxy) benzoic acid derivatives including the salt, alkyl and cycloalkyl esters, alkylthio esters, phenyl ester, alkyl and dialkyl amido and benzoyl chloride forms. Illustrative of those patents are U.S. Pat. Nos. 3,652,645; 3,784,635; 3,873,302; 3,983,168 and 3,907,866.

BRIEF SUMMARY OF THE INVENTION

This invention provides certain herbicidal compounds falling within the general formula: ##STR1## wherein X.sub.1 is halogen, X.sub.2 is selected from halogen and hydrogen, and Z is a polyhalo.sub.1-9 alkyl.sub.1-4 group such as CF.sub.3, CHF.sub.2, C.sub.4 F.sub.9, CF.sub.2 CH.sub.2 CH.sub.3 and CH.sub.2 Cl. Preferably, X.sub.1 is chloro, Z is CF.sub.3 and X.sub.2 is hydrogen. QA in the formula includes certain groups more fully described below.

DETAILED DESCRIPTION

The specific 2-nitro-5-(substituted-phenoxy) benzoyl compounds are described below. One method for preparing these compounds is the use of the Ullman 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 with an active halogen-substituted aromatic, e.g., 3,4-dichlorobenzotrifluoride. The intermediate obtained may be nitrated and subsequently derivatized 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 aforementioned derivatization.

A. Substituted phenyl esters, phenylthio ester, substituted phenylthio esters

Illustrative compounds of this class are those of the formula: ##STR2## where

Q is O or S,

n is an integer from 1 to 5, and

X is selected from NO.sub.2 ; lower alkyl of C.sub.1-4 ; halogen; phenyl; COOR where R is lower alkyl of C.sub.1-4, 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.sub.1-4 ; lower alkoxy of C.sub.1-4 ; trifluoromethyl; and combinations thereof. X can be hydrogen when Q is sulfur.

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-butylphenol (3.60 g, 0.015 mole) and 5-[-2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzoyl chloride (5.68 g, 0.015 mole) in toluene (25 ml) was added triethylamine (1.50 g, 0.015 mole). The temperature exothermed to 45.degree. C. and there was an immediate precipitation of triethylamine hydrochloride. The reaction was stirred and heated to 110.degree. 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 (3.times.25 ml). The toluene was then stripped off on a rotary evaporator to give 5.5 g (62%) of a crude brown oil which slowly crystallized. Recrystallization from methanol gave 2.1 g of an off white solid, mp. 109.degree.-110.degree. C.

I.R. (nujol): C.dbd.O, 1765 cm.sup.-1

NMR (D6 Acetone): triplet 0.9 ppm (3H, J=7.0 Hz): doublet 1.37 ppm (3H, J=7.0 Hz): multiplet 1.82 ppm (2H); multiplet 3.35 ppm (1H); multiplet 7.5-8.2 (5H); doublet 8.45 ppm (1H, J=9.0 Hz); doublet 8.82 ppm (1H, J=2.4 Hz); doublet 9.02 ppm (1H, J=2.4 Hz).

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

______________________________________ Q Phenyl SubstitutionCompound (O or S) X.sub.n m.p., .degree.C.______________________________________2 O 2-NO.sub.2 137-93 O 3-NO.sub.2 93.54 O 4-NO.sub.2 115-75 O 5-CH.sub.3 --2NO.sub.2 88-906 O 2-Cl--4NO.sub.2 99-1017 O 4-Cl 135-78 O 4-Cl--2-CH.sub.3 121-29 O 2-Cl--4-CH.sub.3 105-710 O 2-Cl--4-phenyl 128-3011 O 2,4-(Cl).sub.2 144-712 O 4-COOCH.sub.3 103-613 O 4-CN 103-514 O 4-SCH.sub.3 94-515 O 3-OCH.sub.3 95-716 O 4-OCH.sub.3 128-917 O 3-CF.sub.3 oil18 O 4-COONa 215-2019 O 4-COOH 191-820 S H oil21 S 4-Cl 128-3022 S 4-CH.sub.3 90-323 S 4-OCH.sub.3 oil24 S 3,4-(Cl).sub.2 oil______________________________________

Other compounds of this class include:

______________________________________ ##STR3## Compound______________________________________ ##STR4## 2,6-diethylphenyl 5-[2-chloro-4- (trifluoromethyl) phenyoxy]-2- nitrobenzoate ##STR5## S[2-carboxyphenyl) 5-[2-chloro- 4-(trifluoromethyl) phenoxy]-2- nitrobenzenecarbothioate ##STR6## 4-cyano-2,6-dibromophenyl 5-[2-chloro-4-(trifluoromethyl) phenoxy]-2-nitrobenzoate ##STR7## 3,6-dichloro-2-methoxycarbonyl- phenyl 5-[2-chloro-4- (trifluoromethyl) phenoxy]-2- nitrobenzoate ##STR8## (2,6-di-6-butyl) phenyl 5-[2- chloro-4-(trifluoromethyl) phenoxy]-2-nitrobenzoate ##STR9## pentachlorophenyl 5-[2-chloro- 4-(trifluoromethyl) phenoxy]-2- nitrobenzoate______________________________________

B. Heterocyclic Esters

Illustrative compounds of this class are those of the formula: ##STR10## where Q is O 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-(trifluoromethyl)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.degree. C. 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.degree.-68.degree. C.

I.R. (nujol): C.dbd.O, 1765 cm.sup.-1

NMR(D.sub.6 -acetone): complex multiplet 7.2-8.1 ppm (7H); doublet 8.50 ppm (1H, J=4.5 Hz); multiplet 8.75 ppm (2H).

Compound 26

This compound is defined in accordance with Formula III as "Q" is O and "Het" is ##STR11## The compound was prepared by the procedure shown for Compound 25. Compound 26 has an m.p. of 153.degree.-161.degree. C.

Other compounds of this class include:

______________________________________QHet Compound Name______________________________________ ##STR12## 3-(1,2,5 thiadiazoloyl)-5-[2- chloro-4-trifluoromethyl) phenoxy]-2-nitrobenzoate ##STR13## 1,2-dihydro-1,6-dimethyl-2-oxo 4-pyridinyl 5-[2-chloro-4- trifluoromethyl) phenoxy]-2- nitrobenzoate ##STR14## 6(2,3-dihydro-3-oxo-pyridazinyl) 5-[2-chloro-4-(trifluorom ethyl) phenoxy]-2-nitrobenzoate ##STR15## 2-chloro-6-pyridinyl 5-[2-chloro- 4-(trifluoromethyl) phenoxy]-2- nitrobenzoate ##STR16## s-(2,6-dichloro-4-s-triazinyl) 5-[2-chloro-4-(trifluoromet hyl) phenoxy]-2-nitrobenzoate ##STR17## S(2-methyl 1,3,4,-thiadiazol- 5-yl) 5-[2-chloro-4-trifluo ro- methyl) phenoxy]-2-nitrobenzene- carbothioate ##STR18## S(2-pyridinyl) 5-[-2-chloro-4- (trifluoromethyl) phenoxy]-2- nitrobenzenecarbothioate Noxide ##STR19## S[4-methyl-3-thioxo-3H1,2- dithiol-5-yl] 5-[2-chloro-4- (trifluoromethyl) phenoxy]-2- nitrobenzene-carbothioate ##STR20## S[3,5-bis-(diethylamino)-s-tri- azinyl] 5-[2-chloro-4-(tri fluoro- methyl) phenoxy]-2-nitrobenzene- carbothioate______________________________________

Substituted C.sub.1-4 Alkyl Esters

Illustrative compounds of this class are those of the formula: ##STR21## wherein the substituents on the straight or branched C.sub.1-4 alkyl group are selected from cyano; phenyl; ##STR22## where n is 1 to 5 and X is selected from NO.sub.2, lower alkyl or C.sub.1-4, halogen, phenyl, CN, lower alkyl thio of C.sub.1-4, lower alkoxy of C.sub.1-4, trifluoromethyl and combinations thereof; ##STR23## phenoxy; nitro; SR.sub.1 ; SOR.sub.1 ; SO.sub.2 R.sub.1 ; where R.sub.1 is an alkyl of 1 to 3 carbons and R.sub.2 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.sub.1-4 alkyl group.

The compounds of this class may be prepared by the methods shown above or alternatively by displacement of an active halogen (e.g., Haloalkyl X) with the salt of an acid (e.g., ##STR24##

The following substituted C.sub.1-4 alkyl esters as defined by Formula IV were prepared:

______________________________________Compound Substituted Alkyl Group m.p. .degree.C.______________________________________27 C(CH.sub.3).sub.2 CN oil28 CH(CH.sub.3)CN oil29 CH.sub.2 COCH.sub.3 83-530 ##STR25## oil 31 ##STR26## oil 32 ##STR27## oil 33 ##STR28## oil 34 CH.sub.2CH.sub.2CN oil35 36 ##STR29## 86-8 37 ##STR30## 112-3 38 CH.sub.2 C(CH.sub.3).sub.2NO.sub.2 oily semisolid39 CH.sub.2CH.sub.2SCH.sub.3 oil40 CH.sub.2CH.sub.2SO.sub.2 CH.sub.3 97-9______________________________________

Other compounds of this class include:

______________________________________Substituted alkyl Compound Name______________________________________CH.sub.2SCH.sub.2 CH.sub.3 (ethylthio)methyl 5-[2-chloro-4- (trifluoromethyl) phenoxy]-2- nitro-benzoate ##STR31## (ethylsulfinyl)methyl 5-[2-chloro- 4-(trifluoromethyl) phenoxy]-2- nitro-benzoate ##STR32## (ethylsulfinyl)methyl 5-[2-chloro- 4-(trifluoromethyl) phenoxy]- 2-nitrobenzoate ##STR33## 1-acetylethyl 5-[2-chloro-4-tri- fluoromethyl) phenoxy]-2-nitro- benzoate ##STR34## 3-acetylpropyl 5-[2-chloro-4-(trifluoromethyl) phenoxy]-2-n itrobenzoate ##STR35## 2-(methylsulfinyl) ethyl 5-[2- chloro-4-(trifluoromethyl) phenoxy]-2-nitrobenzoate ##STR36## (3-fluorophenyl) methyl 5-[2-chloro-4-(trifluoromethyl) phenoxy]-2-nitrobenzoate______________________________________

D. Carbonates and Thiocarbonates

Illustrative compounds of this class are those of the formula: ##STR37## where Q is O or S and Y is a straight or branched alkoxy or alkylthio 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-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzoic 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.degree. 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 triethyl amine 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.dbd.O, 1675 and 1800 cm.sup.-1

NMR (CDCl.sub.3): triplet 1.37 ppm (3H, J=7.0 Hz); quartet 3.12 ppm (2H, J=7.0 Hz); complex multiplet 7.0-8.0 ppm (5H); doublet 8.15 ppm (1H, J=9.6 Hz).

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

______________________________________Compound Q Y m.p. .degree.C.______________________________________42 O OCH.sub.3 oil43 O OCH.sub.2 CH.sub.3 oil44 O OCH.sub.2 CH.sub.2 CH.sub.3 oily semi-solid45 O OCH(CH.sub.3).sub.2 oily semi-solid46 O OCH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 oil47 O OCH.sub.2 CH(CH.sub.3).sub.2 oil48 S OCH.sub.3 oil49 S ##STR38## 137-8.degree.______________________________________

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 --SC.sub.3 H.sub.7.

Benzoyl Phosphonates

Illustrative compounds of this class are those of the formula: ##STR39## where R.sub.3 is straight or branched alkyl of 1 to 6 carbons.

Compound 50

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 refluxed for one hour and the disappearance of phosphite monitored by v.p.c.. The ether was stripped off and the resulting oil placed under vacuum (1.0 mm) at 40.degree. C. for two hours. The resulting amber liquid amounted to 5.2 g.

I.R. (neat): C.dbd.O, 1692 and 1730 cm.sup.-1

NMR (CDCl.sub.3): doublet 1.29 ppm (3H, J=6.0 Hz); doublet 1.37 ppm (3H, J=6.0 Hz); multiplet 4.88 ppm (1H); complex multiplet 6.9-8.0 ppm (5H); broad doublet 8.37 ppm (1H, J=9.0 Hz).

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

Compound 51

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

F. Substituted Alkanone Compounds

Illustrative compounds of this class are those of the formula: ##STR40## where A is an alkyl of 1-3 carbons or hydrogen.

Compound 52

Preparation of 5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrophenyl ethanone (A is --CH.sub.3).

A stirred solution of 3-[2-chloro-4-(trifluromethyl)phenoxy]phenyl ethanone (15.7 g, 0.05 mole) in dichloroethane (40 ml) was cooled to 0.5.degree. 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.degree.-10.degree. C. Allowed reaction to warm to room temperature. The progress of the reaction was monitored by v.p.c. The reaction solution was poured onto ice water and the organic 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 solidified to give 8.8 g of a brown solid, m.p. 58.degree.-60.degree. C.

I.R. (nujol mull): C.dbd.O, 1710 cm.sup.-1 ; NO.sub.2, 1530 and 1315 cm.sup.-1.

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.degree.-100.degree. C.

G. Amides

Illustrative compounds of this class include those of the formula: ##STR41## wherein

R.sub.4 is selected from hydrogen and straight or branched chain alkyl of 1-4 carbon:

R.sub.5 is selected from: phenyl; ##STR42## where n is 1 to 5 and X is selected from NO.sub.2, lower alkyl of C.sub.1-4, halogen, phenyl, COOR where R is lower alkyl of C.sub.1-4 or H or a cation, CN, lower alkyl thio of C.sub.1-4, lower alkoxy of C.sub.1-4, trifluoromethyl and combinations thereof; heterocyclicalkyl and heterocyclic, 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; --R.sub.6 CO.sub.2 R.sub.6, where R.sub.6 is an alkyl or alkenyl of up to 3 carbons; --R.sub.6 CONH.sub.2 ; R.sub.6 CON(R.sub.2).sub.2 ; alkoxyalkyl where the alkoxy and alkyl may each contain a straight or branched C.sub.1-3 alkyl chain; or

where R.sub.4 and R.sub.5 together form a heterocyclic ring as hereinabove defined.

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.degree. 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.degree.-4.degree. C. Recrystallization from methanol gave 3.8 g, m.p. 191.degree.-4.degree. C.

I.R. (nujol): C.dbd.O, 1660 cm.sup.-1

NMR (D.sub.6 -Acetone): complex multiplet 7.0-8.1 ppm (10H); doublet 8.32 ppm (1H, J=9.0 Hz); broad singlet 9.95 ppm (1H).

In a similar manner, the following compounds were prepared:

______________________________________Compound R.sub.4 R.sub.5 m.p. .degree.C./oil______________________________________55 H ##STR43## 145-8 56 H ##STR44## 179-81 57 H ##STR45## 155-8 58 H ##STR46## 169-71 59 H ##STR47## 185-7 60 CH(CH.sub.3).sub.2 ##STR48## 144-6 61 H ##STR49## 140-1 62 H OH oil 63 H OCH.sub.3 171-4 64 CH.sub.3 OH oil 65 CH.sub.3 OCH.sub.3 oil 66 H CH.sub.2 COOC.sub.2 H.sub.5 136-7 67 H ##STR50## oil68 H ##STR51## 160-3 69 H CH.sub.2 CH.sub.2 OC.sub.2 H.sub.5 86-8 70 H CH.sub.2 CH.sub.2 CH.sub.2 OCH.sub.3 102-4 71 H ##STR52## 158-60______________________________________Compound R.sub.4 and R.sub.5 m.p. .degree.C./oil______________________________________72 ##STR53## 107-8 73 ##STR54## 128-32 74 ##STR55## 124-6 75 ##STR56## 169-72 76 ##STR57## oil 77 ##STR58## 125-8______________________________________ ##STR59## Compound Name______________________________________ ##STR60## N[2-(5-t-butyl-1,3,4 thiadia- zolyl)]5-[2-chloro-4-(trifl uoro- methyl)phenoxy]-2-nitro- benzamide ##STR61## 5-[2 chloro-4-(trifluoromethyl) phenoxy]-2-nitrobenzoyl 2,5-dioxopyrolidine ##STR62## N[2-(4,6,6-trimethyl-1,3- thiazinyl)]5-[2-chloro-4-(tri- luoromethyl)phenoxy]-2-nitro benzamide ##STR63## N(carboxymethyl)5-[2- chloro-4-(trifluoro- methyl)phenoxy ]-2-nitro benzamide ##STR64## Ncarboxymethyl-Nmethyl 5-[2-chloro-4-(tri- fluoromethyl)p henoxy]-2- nitrobenzamide ##STR65## N(2,5-dichloro-3-methoxy- carbonyl)phenyl 5-[2-chloro-4- trifluoromethyl)phenoxy]- 2-nitrobenzamide ##STR66## N[4-[6-(1,1-dimethylethyl)-3- methylthio-1,2,4-triazin-5( 4H) onyl]]5-[2-chloro-4-(trifluoro- methyl)phenoxy]-2- nitrobenzamide ##STR67## N(3,4-dimethyl-2,6- dinitrophenyl)- N(1-methylethyl) 5-[2-chloro-4-(tri- fluoromethyl)phenoxy]- 2-nitrobenzami de ##STR68## N[2,6-dinitro-4-(tri- fluoromethyl)phenyl]- Nethyl 5-[2-chloro-4- (trifluoromethyl)phenoxy]-2- nitrobenzamid e______________________________________

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:

Compund 78

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

Compound 79 ##STR69## [m.p. 134.degree.-6.degree. C.]

Compound 80

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

Compound 81 ##STR70##

Additional illustrative compounds are listed below according to the structural formula:

__________________________________________________________________________ ##STR71##QA Compound Name__________________________________________________________________________ ##STR72## 4-(2,4-difluorophenyl)-2-(methoxy- carbonyl)phenyl 5-[2-chloro-4-(trifluoromethyl) phenoxy]-2-nitrobenzoa te ##STR73## 4-(ethoxycarbonylethyl)-2-hydroxy- phenyl 5-[2 chloro-4(tri- fluoromethyl)phenoxy]-2- nitrobenzoate ##STR74## 3,5-dinitro-4-dipropylaminophenyl 5-[2-chloro-4-(trifl uoromethyl) phenoxy]-2-nitrobenzoate ##STR75## 2,6-bis(hydroxymethyl)-4-methyl- phenyl 5-[2-chloro-4-(trifluoro- methyl)phenoxy]-2-nitrobenzo ate ##STR76## 3-(1,2,5,6-diisopropylidene-D- glucosyl)5-[2-chloro-4 -(tri- fluoromethyl)phenoxy]-2-nitro- benzoate ##STR77## 2-chloro-9-(methoxycarbonyl) 9Hfluoran-9-yl 5-[2-chloro-4- (trifluoromethyl)phenyl]-2- nitrobenzoa te ##STR78## .alpha.-benzoyl (phenylmethyl)5-[2- chloro-4-(trifluor omethyl)phenoxy]- 2-nitrobenzoate ##STR79## 2-(acetylamino)ethyl 5-[2-chloro- 4-(trifluoromethyl)p henoxy]-2- nitrobenzoate ##STR80## 2-(2-methylpropanoyl- amino)ethyl 5-[ 2-chloro-4- (trifluoromethyl)phenoxy]- 2-nitrobenzoate ##STR81## [3-(dimethylamino)-2-methyl propionyloxy]ethyl 5-[2- chloro-4-(trifluoromethyl) phenoxy]-2-nitrobenzoate ##STR82## 2-(2-methylpropenoyloxy)-2- methylethyl 5-[2-chloro-4-(tri- fluoromethyl)phenoxy]-2-nitro- benzoate ##STR83## (1-cyano-1 methyl)ethoxymethyl 5-[2-chloro-4-(trifluor omethyl) phenoxy]-2-nitrobenzoate ##STR84## (ethoxycarbonyl)(acetyl)methyl 5-[2-chloro-4-(trifluor omethyl) phenoxy]-2-nitrobenzoate ##STR85## diethoxyphosphonylmethyl 5-[2- chloro-4-(trifluorometh yl)phenoxy]- 2-nitrobenzoate ##STR86## dimethoxyphosphonylethyl 5-[2- chloro-4-(trifluorometh yl)phenoxy]- nitrobenzoate ##STR87## dimethoxyphosphonylethoxy ethyl 5-[2-chloro-4-(tri- fluoromethyl) phenoxy]-2-nitrobenzoate ##STR88## 2-(chloroacetyl)ethyl 5-[2-chloro- 4-(trifluoromethyl) phenoxy]-2- nitrobenzoate OCHF.sub.2 difluoromethyl 5-[2-chloro- 4-(trifluoromethyl)phenoxy]-2- nitrobenzoate ##STR89## propenoylaminomethyl 5-[2-chloro- 4-(trifluoromethyl)p henoxy]- 2-nitrobenzoate ##STR90## cyano(ethoxycarbonyl)methyl 5-[2- chloro-4-(trifluorom ethyl)phenoxy]- nitrobenzoate ##STR91## 4-(3-chlorophenylcarbamoyloxy) butyn-2-yl 5-[2-chloro-4- (trifluoromethyl)phenoxy]-2- nitrobenzo ate ##STR92## N(Chloroacetyl)-N(2,6-diethyl- phenylamino)methyl 5-[2-chloro-4-(trifluoromethyl) phenoxy]-2-nitrobenzoa te OCH.sub.2 CHCHCN 3-cyanopropen-2-yl 5-[2-chloro-4-(trifluoromethyl) phenoxy]-2-nitrobenzoateSCN 5-[2-chloro-4-(trifluoromethyl) phenoxy]-2-nitrobenzoic acid anhydride with thiocyanic acid ##STR93## S(phenylsulfonylaminoethyl)5-[2- chloro-4-(trifluorome thyl)phenoxy] 2-nitrobenzenecarbothioate ##STR94## S(2,3-Dihydroxypropyl)5-[2-chloro- 4-(trifluoromethyl) phenoxy]-2- nitrobenzenecarbothioate SCH.sub.2 COOC.sub.2 H.sub.5 S(ethoxycarbonylmethyl)5-[2- chloro-4-(trifluoromethyl) phenoxy]-2-nitrobenzenecarbothioate SCH.sub.2 COOH S(carboxymethyl)5-[2-chloro-4- (trifluoromethyl)phenoxy]-2- nitrobenzenecarbothioate ##STR95## S[(3-fluorophenyl)methyl]5-[2- chloro-4-(trifluorometh yl)phenoxy]- 2-nitrobenzenecarbothioate ##STR96## S[(ethylthiocarbonyl)methyl] 5-[2-chloro-4-(trifluorom ethyl) phenoxy]-2-nitrobenzene- carbothioate ##STR97## S[2,3-dihydroxypropoxycarbonyl) methyl]5-[2-chloro-4-( trifluoro- methyl)phenoxy]-2-nitro- benzenecarbothioat e SCH.sub.2 CHCHCOOC.sub.2 H.sub.5 S[(3-ethoxycarbonyl)propen-2-yl] 5-[2-chloro-4-(trifluoromethyl) phenoxy]-2-nitrobenzene- carbothioate ##STR98## 1,1 dimethyl-2,2,2-trichloro- ethoxycarbonyl 5-[2-chloro-4- (trifluoromethyl)phenoxy]-2- nitrobenzo ate ##STR99## 5-[2-chloro-4-(trifluoromethyl) phenoxy]-2-nitrobenzoy l Oethylphosphonic acid ammonium salt CCl.sub.3 1-{5-[2-chloro-4-(trifluoromethyl) phenoxy]-2-nitrophenyl}2,2,2,- trichloroethanone CF.sub.3 1-{5-[2-chloro-4-(trifluoromethyl) phenoxy]-2-nitrophenyl}2,2,2,- trifluoroethanone ##STR100## dimethyl 5-[2-chloro-4-trifluoro- methyl)phenoxy]-2-ni trobenzoyl- methylphosphonate ##STR101## {5-[2-chloro-4-(trifluoromethyl) phenoxy]2-nitrophenyl }4-methoxy- 3-methylphenyl methanone ##STR102## 1-{5-[2-chloro-4-(trifluoromethyl) phenoxy]-2-nitrophe nyl}2-(di- methoxyphosphonylmethyl- amino)ethanone CN 5-[2-chloro-4-(trifluoromethyl) phenoxy]-2-nitrobenzoyl cyanide__________________________________________________________________________ ______________________________________Miscellaneous - AmideQA Compound Name______________________________________NHCH.sub.2 CH(OCH.sub.3).sub.2 N(2,2-dimethoxyethyl)5- [2-chloro-4-trifluoromethyl) phenoxy]-2-nitrobenzamide ##STR103## N(carboxymethyl)-N (phosphonomethyl)5-[2-chloro-4- (trifluoromethyl)phenoxy]-2- nitrobenzamide ##STR104## N(carboxymethoxy)5-[2-chloro-4- (trifluoromethyl)phenoxy]- 2- nitrobenzamide ##STR105## N(1-methylethyl)-N phenylmethyl)5-[2-chloro-4- (trifluorom ethyl)phenoxy]-2- nitrobenzamide ##STR106## 3{5-[2-chloro-4-(trifluoromethyl) phenoxy]-2-nitrobenzoyl} 4-chloro- 2-oxobenzothiazoline ##STR107## N[1,3-dihydroxy-2-methylpropyl) 5-[2-chloro-4-(trifluorome thyl) phenoxy]-2-nitrobenzamide ##STR108## N(diethoxyphosphonyl)5-[2- chloro-4-(trifluoromethyl)pheno xy]- 2-nitrobenzamide NHCH.sub.2 CH.sub.2 SO.sub. 3 Na N(2-sulfoethyl)5-[2-chloro-4- (trifluoromethyl)phenoxy]-2- nitrobenzamide sodium salt NHCH.sub.2 SO.sub.3 C.sub.6 H.sub.13 N(2-hexyloxysulfonyl)ethyl 5-[2-chloro-4-(trifluoromethyl) phenoxy]-2-nitrobenzamide ##STR109## N(trifluoroacetyl)5-[2-chloro-4- (trifluoromethyl)phenoxy] -2- nitrobenzamide ##STR110## N(4-sulfophenyl)5-[2-chloro- 4-(trifluoromethyl)phenoxy]-2 - nitrobenzamide NHC(CH.sub.3).sub.2 CN N[(1-cyano-1-methyl)-2-ethyl] 4-[2-chloro-4-(trifluoromethyl) phenoxy]-2-nitrobenzamide ##STR111## N(ethoxycarbonyl)5-[2-chloro- 4-(trifluoromethyl)phenoxy]- 2-nitrobenzamide ##STR112## N[2-methyl-4-(phenylsulfonyl) phenyl]5-[2-chloro-4-(triflu oro- methyl)phenoxy]-2-nitrobenzamide ##STR113## N(4-aminophenylsulfonyl)-N (methoxycarbonyl) 5-[2-chloro-4 -(trifluoromethyl) phenoxy]-2-nitrobenzamide NHCHNOH N[(hydroxyimino)methyl] 5-[2-chloro-4-(trifluoromethyl) phenoxy]-2-nitrobenzamide NHNH.sub. 2 5-[2-chloro-4-(trifluoromethyl) phenoxy]-2-nitrobenzoic acid hydrazide ##STR114## 5-[2-chloro-4-(trifluoromethyl) phenoxy]-2-nitrobenzoic acid methyl hydrazide ##STR115## 5-[2-chloro-4-(trifluoromethyl) phenoxy]-2-nitrobenzoyl(2- chloro- acetyl)hydrazide ##STR116## 5-[2-chloro-4-(trifluoromethyl) phenoxy]-2-nitrobenzoyl 2-(carbox- amido)hydrazide NHCN 5-[2-chloro-4-(trifluoromethyl)- phenoxy]-2-nitrobenzoylcyanamide ##STR117## 5-[2-chloro-4-(trifluoromethyl)- phenoxy]-2-nitrobenzoylcy anamide sodium salt N.sub.3 5-[2-chloro-4-(trifluoromethyl) phenoxy]-2-nitrobenzoyl amide ONCHNH.sub.2 aminomethyleneamino 5-[2-chloro- 4-(trifluoromethyl)phenoxy]-2 nitrobenzoate ONC(CH.sub.3).sub.2 1-methylethylideneimino 5-[2- chloro-4-(trifluoromethyl) phenoxy]-2-nitrobenzoate ##STR118## 1-(methylthio)ethylideneamino 5[2-chloro-4-(trifluoromethy l) phenoxy]-2-nitrobenzoate______________________________________

Primary Herbicide Screening

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 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 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.

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 0.03 pounds and about 10 pounds per acre.

HERBICIDAL EFFECTIVENESS

Method of Propagating Test Species

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

Cotton, corn, soybean, and cocklebur plantings consist of 4 to 5 seeds per row depending upon species. The smaller seeded species (velvetleaf, wild mustard, pigweed, foxtail millet and green foxtail) 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 for the pre-emergence phase are made not more than one day in advance of treatment.

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

Spray applications are made with a handgun sprayer (aspirator type) simultaneously to one flat of 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%.

Following spray application, flats are returned to the greenhouse where watering of the post-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.

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

______________________________________Application RateUS - lb./acre Metric - kg/ha______________________________________10.0 11.24.0 4.482.0 2.241.0 1.120.5 0.560.25 0.28______________________________________

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

TABLE I__________________________________________________________________________ DosageCpd. Lbs./ Pre-EmergenceNo. Acre CG FM GF VL CB WM PW CT CN SB__________________________________________________________________________1 10 -- 100 90 90 0 100 100 10 0 0 4 -- 100 90 20 -- 100 -- 0 0 0 2 -- 100 60 10 -- 100 70 0 10 10 1 -- 90 90 30 0 100 100 20 0 10 1/2 -- 90 80 0 0 90 100 20 0 10 1/4 -- 90 70 30 0 90 80 0 10 02 10 -- 20 20 10 0 70 90 0 0 0 4 -- -- -- -- -- -- -- -- -- -- 2 -- -- -- -- -- -- -- -- -- -- 1 -- -- -- -- -- -- -- -- -- -- 1/2 -- -- -- -- -- -- -- -- -- -- 1/4 -- -- -- -- -- -- -- -- -- --3 10 -- 90 90 0 0 90 100 0 0 0 4 -- 100 90 30 20 90 100 10 0 0 2 -- 60 10 0 10 30 80 -- 0 0 1 -- -- -- -- -- -- -- -- -- -- 1/2 -- -- -- -- -- -- -- -- -- -- 1/4 -- -- -- -- -- -- -- -- -- --4 10 -- 100 90 90 20 100 100 10 0 10 4 -- 100 90 0 -- 100 -- 0 0 10 2 -- 90 40 0 -- 70 60 0 0 0 1 -- -- -- -- -- -- -- -- -- -- 1/2 -- -- -- -- -- -- -- -- -- -- 1/4 -- -- -- -- -- -- -- -- -- --5 4 -- 90 90 70 30 100 100 60 0 0 2 -- 90 90 10 40 100 100 20 0 10 1 -- 70 10 0 0 70 100 0 0 10 1/2 -- -- -- -- -- -- -- -- -- -- 1/4 -- -- -- -- -- -- -- -- -- --6 4 -- 100 90 70 20 100 100 0 40 0 2 -- 100 90 10 0 100 100 40 0 0 1 -- 90 60 0 40 90 90 30 0 0 1/2 -- 70 80 10 0 50 90 10 0 10 1/4 -- 20 0 10 10 30 0 0 20 107 4 -- 0 0 0 0 100 100 40 0 0 2 -- 70 20 0 0 0 70 0 0 0 1 -- -- -- -- -- -- -- -- -- -- 1/2 -- -- -- -- -- -- -- -- -- -- 1/4 -- -- -- -- -- -- -- -- -- --8 10 -- 0 0 0 0 0 0 0 30 0 4 -- -- -- -- -- -- -- -- -- -- 2 -- -- -- -- -- -- -- -- -- --9 4 -- 0 0 0 -- 10 60 10 0 0 2 -- -- -- -- -- -- -- -- -- -- 1 -- -- -- -- -- -- -- -- -- -- 1/2 -- 10 0 0 0 50 60 0 0 0 1/4 -- -- -- -- -- -- -- -- -- --10 4 -- 10 10 10 0 0 0 10 10 10 2 -- -- -- -- -- -- -- -- -- --11 10 -- 0 0 0 0 0 0 0 0 0 4 -- -- -- -- -- -- -- -- -- --12 4 -- 100 90 90 60 100 100 40 10 0 2 -- 100 90 40 10 100 100 10 30 0 1 -- 100 90 0 0 100 100 0 0 0 1/2 -- 70 30 10 0 90 90 30 0 0 1/4 -- 20 20 0 0 20 60 60 60 3013 10 -- 90 90 100 80 100 100 90 10 10 4 -- 90 90 70 10 90 90 10 20 0 2 -- 90 70 30 0 90 90 0 0 0 1 -- -- -- -- -- -- -- -- -- -- 1/2 -- -- -- -- -- -- -- -- -- -- 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 90 10 0 0 2 -- 90 90 10 0 90 90 0 0 0 1 -- 70 60 10 0 20 80 20 0 10 1/2 -- -- -- -- -- -- -- -- -- -- 1/4 -- -- -- -- -- -- -- -- -- --16 4 -- 90 50 10 0 90 70 10 10 0 2 -- 80 10 10 0 70 0 0 0 10 1 -- -- -- -- -- -- -- -- -- -- 1/2 -- -- -- -- -- -- -- -- -- -- 1/4 -- -- -- -- -- -- -- -- -- --17 4 -- 100 90 40 0 100 100 0 10 0 2 -- 90 90 30 0 90 90 30 0 10 1 -- -- -- -- -- -- -- -- -- -- 1/2 -- -- -- -- -- -- -- -- -- -- 1/4 -- -- -- -- -- -- -- -- -- --18 10 -- 100 80 70 0 100 100 10 0 0 2 -- 100 40 20 10 100 100 10 0 10 1/2 -- 90 20 0 10 100 90 10 10 30 1/4 -- 10 10 40 10 80 60 10 0 019 10 -- 100 100 80 60 100 100 30 60 0 2 -- 100 70 40 10 100 100 20 10 10 1/2 -- 100 60 0 0 100 60 10 0 0 1/4 -- 10 10 60 20 70 50 20 0 2020 4 -- 90 80 50 0 100 90 0 0 0 2 -- 80 20 10 20 90 20 0 0 10 1 -- 0 0 0 0 0 20 30 10 10 1/2 -- -- -- -- -- -- -- -- -- -- 1/4 -- -- -- -- -- -- -- -- -- --21 4 -- 80 60 20 0 30 20 10 20 20 2 -- -- -- -- -- -- -- -- -- --22 4 -- 90 80 20 0 90 90 0 10 0 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 0 2 -- 70 10 30 0 70 10 0 0 0 1/2 -- -- -- -- -- -- -- -- -- -- 1/4 -- -- -- -- -- -- -- -- -- --24 4 -- 90 70 60 10 90 90 0 0 10 2 -- 80 70 40 0 70 80 0 0 0 1/2 -- 0 10 0 0 0 10 0 0 0 1/4 -- -- -- -- -- -- -- -- -- --25 4 -- 100 90 90 20 100 100 10 40 10 2 -- 90 90 80 40 100 100 40 10 20 1 -- 100 90 10 0 90 90 0 0 0 1/2 -- 90 70 0 0 90 70 10 0 10 1/4 -- 10 20 10 0 20 20 0 0 026 2 -- 40 40 20 70 90 70 0 0 10 1/2 -- 10 0 10 0 90 40 0 0 0 1/4 -- -- -- -- -- -- -- -- -- --27 2 -- 90 90 80 0 100 100 10 0 0 1/2 -- 70 50 40 0 90 100 0 0 0 1/4 -- 50 10 0 0 70 10 0 0 028 2 -- 90 90 90 20 100 100 50 10 20 1/2 -- 90 90 20 0 100 100 10 0 0 1/4 -- 60 20 0 -- 50 80 10 0 029 2 -- 100 100 40 10 100 100 0 0 20 1/2 -- 100 90 0 0 100 90 10 0 0 1/4 -- 10 40 60 0 90 90 0 0 030 1/2 10 60 -- 30 -- 90 90 -- -- -- 1/4 10 40 -- 10 -- 10 -- -- -- --31 2 -- 60 50 10 0 80 90 30 20 0 1/2 -- 10 0 10 0 10 50 0 0 0 1/4 -- -- -- -- -- -- -- -- -- --32 2 -- 90 70 0 0 100 100 10 0 10 1/2 -- 90 90 0 0 90 80 0 0 10 1/4 -- 30 10 0 0 10 0 0 0 033 2 -- 100 90 50 0 90 90 10 10 40 1/2 -- 80 10 0 0 20 10 0 0 0 1/4 -- -- -- -- -- -- -- -- -- --34 2 -- 100 100 10 30 90 90 30 10 0 1/2 -- 20 20 20 10 80 20 0 0 0 1/4 -- -- -- -- -- -- -- -- -- --36 2 -- 50 20 40 -- 20 90 10 20 30 1/2 -- 0 0 0 -- 20 50 10 10 10 1/4 -- -- -- -- -- -- -- -- -- --37 2 -- 60 60 0 -- 80 20 0 0 0 1/2 -- 0 0 0 -- 0 0 0 0 0 1/4 -- -- -- -- -- -- -- -- -- --38 2 -- 100 90 50 10 100 100 60 0 0 1/2 -- 90 50 0 0 50 40 0 0 0 1/4 -- -- -- -- -- -- -- -- -- --39 2 -- 90 90 70 20 100 100 10 20 0 1/2 -- 90 70 10 10 100 100 0 0 040 2 -- 100 90 90 0 100 100 10 10 0 1/2 -- 90 70 20 0 100 90 10 0 041 2 -- 100 90 40 0 100 90 10 0 0 1/2 -- 90 30 0 0 90 70 0 0 0 1/4 -- 0 0 0 0 10 10 0 0 042 2 -- 100 100 90 70 100 100 90 20 30 1/2 -- 100 100 80 60 100 100 90 20 30 1/4 -- 80 90 10 0 60 90 10 0 1043 1/2 90 90 -- 50 0 90 100 -- -- -- 1/4 60 90 -- 50 -- 10 -- -- -- --44 2 -- 100 100 90 30 100 100 60 20 30 1/2 -- 90 90 80 10 100 100 20 10 20 1/4 -- 20 0 0 0 90 20 0 0 1045 2 -- 100 100 70 10 100 100 10 10 0 1/2 -- 90 80 10 0 100 100 0 0 0 1/4 -- 90 10 0 0 80 90 0 0 046 2 -- 100 90 20 10 100 90 10 0 0 1/2 -- 90 90 10 30 90 70 10 0 0 1/4 -- 30 20 0 0 0 0 0 0 047 2 -- 100 90 90 20 100 100 30 10 0 1/2 -- 100 90 20 10 100 100 10 0 0 1/4 -- 20 0 0 0 90 90 20 10 048 2 -- 100 100 70 100 100 0 0 0 0 1/2 -- 100 90 30 0 90 60 40 0 049 2 -- 90 90 60 0 90 100 0 0 0 1/2 -- 20 0 10 10 100 90 0 0 1050 2 -- 90 90 90 50 100 100 50 10 30 1 -- 90 90 20 0 100 90 0 0 0 1/2 -- 80 70 10 0 100 90 10 10 20 1/4 -- 90 70 20 10 90 80 0 0 051 10 -- 100 100 100 50 100 100 10 30 0 4 -- 100 100 90 60 100 100 20 10 20 2 -- 90 90 70 10 100 100 20 0 10 1 -- 100 100 10 0 100 100 0 0 10 1/2 -- 90 50 0 10 70 40 0 0 0 1/4 -- -- -- -- -- -- -- -- -- --52 10 100 100 -- 90 -- 100 -- -- -- -- 1 60 70 -- 60 0 90 -- -- -- -- 1/2 40 80 -- 50 10 80 -- -- -- -- 1/4 -- -- -- -- -- -- -- -- -- --53 10 -- 90 90 50 -- 100 100 50 10 0 4 -- 90 90 30 -- 100 100 10 0 0 1 -- 90 60 0 -- 90 90 0 0 0 1/2 -- 10 0 10 -- 20 90 0 0 0 1/4 -- -- -- -- -- -- -- -- -- --54 4 -- 0 0 0 0 0 0 0 0 0 2 -- -- -- -- -- -- -- -- -- -- 1 -- -- -- -- -- -- -- -- -- -- 1/2 -- -- -- -- -- -- -- -- -- -- 1/4 -- -- -- -- -- -- -- -- -- --55 4 -- 0 20 40 10 90 100 60 0 20 2 -- 0 0 0 0 0 0 0 0 0 1 -- -- -- -- -- -- -- -- -- -- 1/2 -- -- -- -- -- -- -- -- -- -- 1/4 -- -- -- -- -- -- -- -- -- --56 4 -- 0 0 30 -- 70 100 30 0 0 2 -- -- -- -- -- -- -- -- -- --57 4 -- 10 0 0 -- 70 90 0 0 0 2 -- -- -- -- -- -- -- -- -- -- 1 -- -- -- -- -- -- -- -- -- -- 1/2 -- -- -- -- -- -- -- -- -- -- 1/4 -- -- -- -- -- -- -- -- -- --58 4 -- 30 0 0 -- 10 100 0 0 0 2 -- -- -- -- -- -- -- -- -- -- 1 -- -- -- -- -- -- -- -- -- --59 10 -- 0 0 0 -- 0 100 0 0 060 10 -- 0 0 10 0 10 70 0 0 0 4 -- -- -- -- -- -- -- -- -- --61 2 -- 50 20 60 10 90 80 20 10 20 1/2 -- 0 0 0 0 50 0 0 0 0 1/4 -- -- -- -- -- -- -- -- -- --62 4 90 100 -- 80 -- 100 100 -- -- -- 1 90 40 -- 70 -- 100 100 -- -- -- 1/2 40 0 -- 10 0 80 -- -- -- --63 4 90 90 -- 100 -- 100 100 -- -- -- 1 60 40 -- 70 -- 90 0 -- -- -- 1/2 20 0 -- 20 0 10 0 -- -- --64 4 90 90 -- 90 -- 100 100 -- -- -- 2 90 90 -- 50 -- 100 90 -- -- -- 1 20 0 -- 40 0 90 0 -- -- -- 1/2 0 20 -- 0 0 70 70 -- -- --65 4 80 90 -- 90 -- 100 -- -- -- -- 2 -- 30 70 20 0 80 100 0 0 0 1 -- 90 70 80 0 90 90 10 10 0 1/2 -- 10 10 50 0 100 100 0 0 0 1/4 -- 30 10 10 0 70 80 0 0 066 4 90 90 -- 100 -- 100 100 -- -- -- 1 70 40 -- 70 -- 100 100 -- -- -- 1/2 0 10 -- 20 0 60 0 -- -- --67 4 90 90 -- 90 -- 100 100 -- -- -- 2 60 70 -- 60 -- 90 90 -- -- -- 1 0 0 -- 10 0 40 0 -- -- -- 1/2 0 0 -- 40 10 90 20 -- -- --68 10 100 90 -- 100 -- 100 100 -- -- -- 4 -- 100 90 90 60 100 100 0 10 0 2 -- 90 90 90 10 100 100 20 20 20 1 -- 90 30 90 0 100 100 40 0 0 1/2 -- 70 80 70 50 100 100 10 0 0 1/4 -- 80 60 0 0 100 100 20 0 --69 2 -- 100 90 60 50 100 100 10 40 20 1/2 -- 100 90 10 10 100 100 0 0 10 1/4 -- 0 60 10 10 80 80 10 50 1070 2 -- 100 90 50 50 100 100 10 10 20 1/2 -- 100 90 10 30 100 100 20 0 10 1/4 -- 0 10 50 0 90 90 0 40 8071 2 -- 90 50 40 0 90 80 10 10 10 1/2 -- 10 10 0 0 10 90 10 0 10 1/4 -- -- -- -- -- -- -- -- -- --72 10 -- 90 90 -- 20 90 90 -- 40 70 2 -- 90 90 70 0 100 100 10 20 0 1 -- 90 80 0 0 90 80 10 0 0 1/2 -- 20 0 10 -- 90 90 20 20 10 1/4 -- 30 0 10 -- 70 80 0 20 1073 10 -- 100 90 90 30 100 100 20 60 0 4 -- 100 90 80 60 100 90 50 70 10 2 -- 80 70 70 10 100 10 10 0 0 1 -- 90 60 10 0 90 60 20 0 10 1/2 -- 90 50 0 0 90 80 0 0 074 2 -- 90 90 70 0 100 100 10 10 0 1/2 -- 90 70 0 0 90 50 10 0 0 1/4 -- 0 0 10 0 70 70 10 0 1075 2 -- 60 20 0 0 50 80 0 0 0 1 -- -- -- -- -- -- -- -- -- -- 1/2 -- -- -- -- -- -- -- -- -- -- 1/4 -- -- -- -- -- -- -- -- -- --76 2 -- 80 40 80 0 70 70 20 60 10 1/2 -- 10 10 0 0 70 70 10 0 0 1/4 -- -- -- -- -- -- -- -- -- --77 2 -- 100 90 10 0 100 90 0 0 0 1/2 -- 90 70 0 10 90 60 10 0 078 10 90 90 -- 100 -- 100 -- -- -- -- 4 -- 90 90 90 0 100 100 0 0 0 2 -- 90 90 80 0 90 100 10 0 0 1 -- 40 60 60 10 100 100 0 0 0 1/2 -- 50 70 0 -- 90 90 0 0 0 1/4 -- 80 50 20 0 90 60 10 30 079 10 70 90 -- 50 -- 90 -- -- -- -- 1/4 0 0 -- 0 -- 0 -- -- -- --80 4 -- 100 90 40 20 90 90 0 20 10 2 -- 90 80 10 10 90 10 10 10 10 1 -- 10 0 0 0 70 20 0 0 0 1/2 -- -- -- -- -- -- -- -- -- -- 1/4 -- -- -- -- -- -- -- -- -- --81 2 -- 80 50 0 0 90 80 0 0 0 1/2 -- 10 0 0 0 10 60 0 0 0 1/4 -- -- -- -- -- -- -- -- -- --__________________________________________________________________________ TABLE II__________________________________________________________________________ DosageCpd. Lbs./ Post-EmergenceNo. Acre CG FM GF VL CB WM PW CT CN SB__________________________________________________________________________1 10 -- 100 100 100 100 100 100 100 80 60 4 -- 90 90 100 100 100 100 90 60 50 2 -- 100 100 100 -- 100 -- 90 50 20 1 -- 100 90 100 -- 100 100 90 30 50 1/2 -- 100 90 90 90 100 100 80 70 10 1/4 -- 50 50 40 80 100 100 60 50 402 10 -- 90 90 90 80 90 100 90 10 10 4 -- 100 90 90 60 90 90 90 10 10 2 -- 90 90 90 80 100 100 90 20 20 1 -- 90 90 80 90 90 100 90 70 70 1/2 -- 80 70 60 90 100 100 90 80 30 1/4 -- 90 70 70 80 100 80 90 50 603 10 -- 90 90 90 90 100 100 100 30 30 4 -- 100 100 90 90 100 100 90 30 10 2 -- 100 90 100 90 100 100 90 90 20 1 -- 90 90 90 90 100 100 80 70 60 1/2 -- 90 90 90 90 100 90 90 90 60 1/4 -- 90 80 90 80 100 100 90 30 104 10 -- 100 100 100 100 100 100 100 90 50 4 -- 100 100 100 -- 100 -- 100 90 30 2 -- 90 90 100 100 100 100 100 20 20 1 -- 100 100 100 -- 100 100 100 40 50 1/2 -- 100 90 90 90 100 100 100 70 10 1/4 -- 50 70 30 50 90 100 40 30 505 4 -- 100 90 100 100 100 100 90 0 40 2 -- 90 90 100 -- 100 -- 90 10 20 1 -- 90 90 100 0 100 100 90 50 10 1/2 -- 80 70 90 80 100 100 90 20 20 1/4 -- 60 60 50 70 90 100 60 30 606 4 -- 100 100 100 100 100 100 100 10 60 2 -- 100 100 100 100 100 100 90 80 40 1 -- 70 80 70 70 100 100 60 70 60 1/2 -- 90 90 90 90 100 90 80 80 20 1/4 -- 80 60 80 50 90 70 90 10 107 4 -- 100 80 100 80 100 100 80 0 20 2 -- 90 30 100 -- 90 100 90 10 20 1 -- 90 70 100 -- 90 100 90 -- 40 1/2 -- 90 90 100 -- 90 100 90 10 50 1/4 -- 90 90 90 50 100 100 60 30 408 10 -- 90 80 100 60 90 100 40 0 20 4 -- 60 30 -- -- 70 -- 70 20 0 2 -- 80 70 50 -- 70 70 90 0 109 4 -- 90 90 100 40 90 100 90 10 20 2 -- 90 90 90 -- 90 100 90 10 30 1 -- 90 90 100 80 100 100 90 0 10 1/2 -- 100 90 90 70 100 100 80 10 10 1/4 -- 70 80 30 50 90 100 50 50 4010 4 -- 80 20 70 10 90 50 90 40 10 2 -- 50 50 70 0 90 70 90 70 3011 10 -- 90 90 70 30 80 100 40 0 10 4 -- 30 20 30 20 70 90 80 30 1012 4 -- 90 90 100 90 100 100 90 20 10 2 -- 100 100 90 100 100 100 100 70 40 1 -- 100 100 100 100 100 100 100 60 10 1/2 -- 100 100 90 80 100 100 80 80 60 1/4 -- 90 90 90 70 100 100 90 60 5013 10 -- 90 90 100 100 100 100 90 80 20 4 -- 100 100 100 100 100 100 100 90 90 2 -- 100 100 90 90 100 100 100 90 50 1 -- 90 90 90 70 100 100 90 70 50 1/2 -- 90 90 80 70 100 100 90 70 60 1/4 -- 90 80 80 80 100 90 90 60 6014 4 -- 90 90 90 80 100 100 90 30 20 1 -- 90 90 80 10 90 90 90 70 40 1/2 -- 90 90 70 70 90 90 80 70 20 1/4 -- 80 80 70 50 90 100 80 50 7015 4 -- 90 100 100 90 100 100 100 60 10 2 -- 90 90 90 90 100 90 90 70 30 1 -- 90 90 80 60 90 100 90 50 30 1/2 -- 90 90 90 90 100 100 90 50 30 1/4 -- 90 70 60 50 70 90 70 50 7016 4 -- 90 90 60 50 100 100 90 50 10 2 -- 30 40 60 30 90 80 70 50 80 1 -- 70 60 70 70 90 90 90 60 70 1/2 -- 90 70 70 80 100 100 90 60 40 1/4 -- 60 40 60 30 90 100 60 50 5017 4 -- 100 100 100 90 100 100 90 70 30 2 -- 100 100 100 90 100 100 100 80 40 1 -- 90 90 80 60 90 100 70 70 40 1/2 -- 90 90 90 90 90 90 90 70 10 1/4 -- 80 80 80 50 90 60 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-- -- -- -- -- -- -- -- -- 1 -- 100 100 100 90 100 90 100 90 70 1/2 -- 90 90 90 90 100 100 100 90 90 1/4 -- 80 80 90 80 90 90 90 40 3026 2 -- 50 70 100 90 100 100 90 30 60 1/2 -- 10 0 90 50 90 90 50 20 40 1/4 -- 20 10 60 80 90 100 50 10 5027 2 -- 100 100 100 100 100 100 90 70 90 1/2 -- 100 100 100 90 100 100 90 60 60 1/4 -- 70 60 90 70 100 60 90 50 8028 2 -- 100 90 100 100 100 100 100 90 90 1/2 -- 90 90 90 90 100 100 90 90 60 1/4 -- 90 90 90 80 100 100 100 70 8029 2 -- 100 100 100 90 100 100 100 60 90 1/2 -- 90 90 100 80 100 100 90 10 80 1/4 -- 90 90 100 70 100 100 90 50 8030 1/2 20 100 -- -- -- 100 100 90 80 60 1/4 90 90 -- 70 100 100 100 90 20 4031 2 -- 90 90 100 90 100 100 90 30 60 1/2 -- 90 90 100 70 90 100 90 60 30 1/4 -- 80 80 100 60 80 100 80 30 7032 2 -- 100 100 100 90 100 100 100 40 80 1/2 -- 100 100 100 80 100 100 100 20 80 1/4 -- 30 20 100 90 90 90 70 60 4033 2 -- 100 100 100 90 100 100 100 70 80 1/2 -- 90 90 100 70 100 100 100 70 80 1/4 -- 80 70 90 90 100 100 70 10 4034 2 -- 70 70 100 90 100 100 90 60 60 1/2 -- 60 60 100 90 100 100 80 40 40 1/4 -- 90 70 90 90 100 100 50 20 5036 2 -- 100 90 90 80 100 100 90 90 50 1/2 -- 90 90 90 30 90 100 90 70 60 1/4 -- 20 30 90 -- 90 90 90 40 1037 2 -- 90 90 80 0 90 90 90 80 70 1/2 -- 90 90 90 -- 90 90 90 40 40 1/4 -- 10 10 70 -- 80 70 50 10 3038 2 -- 90 90 100 90 100 100 90 50 60 1/2 -- 90 90 100 90 100 100 60 10 50 1/4 -- 30 20 90 80 100 100 70 10 1039 2 -- 90 90 100 100 100 100 100 60 90 1/2 -- 90 90 90 90 100 100 100 40 7040 2 -- 100 100 100 100 100 100 100 90 90 1/2 -- 90 90 100 90 100 100 100 30 7041 2 -- 100 100 100 100 100 100 100 90 90 1/2 -- 90 90 100 90 100 90 90 30 80 1/4 -- 70 80 90 70 100 90 90 20 6042 2 -- 100 100 100 100 100 100 100 100 90 1/2 -- 100 100 90 90 100 100 100 90 90 1/4 -- 100 100 100 80 100 100 90 50 8043 1/2 70 100 -- 90 100 100 100 100 40 40 1/4 100 100 -- 90 100 100 100 70 40 3044 2 -- 100 100 100 100 100 100 100 90 90 1/2 -- 100 100 100 90 100 100 90 80 80 1/4 -- 90 90 90 70 100 100 90 60 6045 2 -- 100 100 100 100 100 100 100 100 90 1/2 -- 100 100 90 90 100 100 100 80 60 1/4 -- 100 100 90 90 100 100 90 50 6046 2 -- 100 100 100 90 100 100 100 90 90 1/2 -- 100 100 100 70 90 90 100 70 50 1/4 -- 90 90 90 30 90 90 90 50 5047 2 -- 100 100 100 100 100 100 100 90 80 1/2 -- 90 90 70 90 100 100 90 50 30 1/4 -- 90 90 60 20 100 100 80 20 6048 2 -- 100 100 100 90 100 100 100 90 80 1/2 -- 90 90 90 90 100 100 100 40 9049 2 -- 50 10 90 70 100 100 60 20 30 1/2 -- 10 20 70 30 100 100 90 40 3050 2 -- 90 90 60 90 100 100 90 70 40 1 -- 90 90 100 100 100 100 80 90 60 1/2 -- 60 80 90 70 100 100 80 0 10 1/4 -- 90 80 90 70 100 100 40 0 3051 10 -- 100 100 100 80 100 100 90 70 70 4 -- 100 100 100 100 100 100 90 90 70 2 -- 90 90 100 90 100 100 90 70 40 1 -- 100 100 100 100 100 100 80 90 80 1/2 -- 60 80 100 80 100 100 90 10 20 1/4 -- 100 90 100 70 100 90 50 0 4052 10 70 90 -- 100 -- 100 100 80 30 30 1 70 40 -- 100 50 100 100 80 10 40 1/2 30 20 -- 70 20 90 100 40 10 10 1/4 20 90 -- 30 20 100 100 70 30 1053 10 100 100 -- 100 90 100 100 100 90 90 4 100 90 -- 80 80 100 100 100 70 80 1 90 90 -- 70 60 100 100 90 60 50 1/2 40 40 -- 20 0 100 90 80 20 50 1/4 20 10 -- 10 -- 90 50 20 10 3054 4 -- 30 30 80 30 100 100 40 10 10 2 -- 20 20 10 -- 90 90 20 10 10 1 -- 80 80 90 40 90 90 50 10 20 1/2 -- 60 50 10 -- 90 90 30 10 10 1/4 -- 20 40 30 50 80 60 40 40 1055 4 -- 20 20 10 20 100 100 -- 0 10 2 -- 30 30 0 -- 100 80 20 0 80 1 -- 80 80 20 30 90 100 30 20 30 1/2 -- 80 80 10 -- 90 -- 80 0 10 1/4 -- 20 30 0 30 30 30 0 0 1056 4 -- 80 90 50 70 100 100 20 20 10 2 -- 30 10 30 -- 60 80 70 0 1057 4 -- 60 80 40 30 90 100 70 0 10 2 -- 70 40 0 -- 100 100 60 10 10 1 -- 60 50 0 -- 90 90 60 40 30 1/2 -- 20 30 20 -- 90 100 50 10 20 1/4 -- 20 20 10 30 60 80 50 10 1058 4 -- 40 70 0 40 90 100 30 -- 20 2 -- 10 10 0 -- 90 100 10 0 10 1 -- 50 50 30 20 70 100 30 20 3059 10 -- 0 10 0 0 0 80 0 0 060 10 -- 80 60 10 70 90 100 30 10 10 4 -- 20 10 10 20 80 70 50 0 1061 2 -- 30 20 90 60 100 100 80 30 30 1/2 -- 20 30 80 50 100 100 70 20 30 1/4 -- 60 60 90 70 90 100 40 20 3062 4 20 20 -- 0 20 100 -- 30 10 20 1 0 10 -- 10 10 60 70 30 0 30 1/2 30 30 -- 0 10 70 50 10 0 2063 4 0 0 -- 0 0 90 -- 20 20 30 1 0 30 -- 20 10 50 80 10 10 20 1/2 20 0 -- 0 0 70 60 10 0 3064 4 0 20 -- 10 30 30 100 60 10 10 2 0 10 -- 20 10 100 90 70 10 10 1 20 20 -- 10 20 80 50 20 0 10 1/2 10 10 -- 10 10 80 60 0 10 2065 4 10 20 -- 30 -- 100 100 70 20 40 2 -- 70 90 100 90 100 100 90 20 10 1 -- 90 90 100 90 100 100 80 30 40 1/2 -- 90 90 90 -- 90 100 20 10 10 1/4 -- 50 40 70 70 90 100 80 30 4066 4 0 40 -- 10 20 90 100 20 40 30 1 0 0 -- 10 50 60 50 70 0 40 1/2 10 10 -- 20 40 40 50 10 0 4067 4 20 20 -- 10 60 40 100 50 40 50 2 10 10 -- 30 50 100 100 80 10 20 1 20 20 -- 0 10 20 100 20 10 40 1/2 20 0 -- 10 40 30 100 10 20 2068 10 20 20 -- 30 -- 100 100 90 20 50 4 -- 100 100 100 100 100 100 90 90 60 2 -- 100 90 100 100 100 100 80 60 90 1 -- 30 50 100 -- 90 100 90 20 30 1/2 -- 90 90 100 -- 90 100 90 70 90 1/4 -- 50 40 80 80 90 100 70 30 6069 2 -- 100 90 100 80 100 100 90 80 70 1/2 -- 90 90 100 70 90 90 70 40 70 1/4 -- 50 40 100 60 90 90 90 50 6070 2 -- 90 80 100 70 100 100 90 70 60 1/2 -- 90 80 100 60 100 100 90 20 50 1/4 -- 90 70 100 50 90 90 80 20 4071 2 -- 40 60 100 90 100 100 90 20 60 1/2 -- 40 40 100 90 100 100 90 10 50 1/4 -- 20 10 60 80 90 100 50 10 5072 10 -- 100 100 100 100 100 100 100 90 80 2 -- 100 100 100 90 100 100 100 80 80 1 -- 100 100 100 90 100 100 100 80 80 1/2 -- 90 90 90 90 100 100 90 50 80 1/4 -- 90 90 90 80 100 100 100 30 8073 10 -- 100 100 100 70 100 100 90 80 50 4 -- 90 90 100 90 100 100 90 70 40 2 -- 30 50 70 40 100 100 50 10 30 1 -- 40 40 50 70 90 100 50 20 30 1/2 -- 90 90 80 70 100 100 70 20 2074 2 -- 90 80 90 10 100 100 90 10 40 1/2 -- 90 80 90 -- 100 90 90 20 30 1/4 -- 60 60 80 90 90 90 90 10 4075 2 -- 80 70 60 20 90 100 90 10 20 1 -- 90 80 80 40 100 70 70 20 20 1/2 -- 20 20 50 10 90 90 90 10 10 1/4 -- 10 10 70 -- 60 20 50 0 2076 2 -- 20 10 40 -- 90 100 90 10 50 1/2 -- 10 10 10 -- 90 90 60 10 40 1/4 -- 10 10 80 30 80 70 40 10 1077 2 -- 90 90 100 90 100 100 50 20 30 1/2 -- 90 90 90 80 100 100 30 10 3078 10 60 20 -- 70 -- 100 100 90 70 30 4 -- 80 90 100 90 100 100 90 0 10 2 -- 100 100 100 90 100 100 90 50 70 1 -- 90 90 100 60 100 100 40 80 40 1/2 -- 90 90 90 80 90 -- 30 20 20 1/4 -- 40 80 40 50 80 100 40 40 4079 10 50 60 -- 80 -- 100 100 80 10 20 1/2 70 80 -- 40 80 90 100 70 10 1080 4 -- 90 90 100 50 100 90 90 90 30 2 -- 70 50 90 50 90 60 90 60 90 1 -- 70 70 80 20 90 90 90 40 10 1/2 -- 30 30 70 50 90 90 90 60 20 1/4 -- 50 50 40 50 80 100 50 20 5081 2 -- 40 40 90 70 100 100 90 30 60 1/2 -- 30 30 100 50 100 100 90 10 40 1/4 -- 40 40 90 30 90 90 50 10 30__________________________________________________________________________

Although the present invention has been described with preferred embodiments, it is to be understood that modifications and variations may be resorted to, without departing from the spirit and scope of this invention, as those skilled in the art will readily understand. Such modifications and variations are considered to be within the purview and scope of the appended claims.

Claims

1. A herbicidal compound of the formula: ##STR119## wherein Q is O or S and Het is a heterocyclic ring selected from the group consisting of s-triazinyl; 2,3-dihydro-pyridazinyl; 1,2,5-thiadiazolyl; 1,3,4-thiadiazol-5-yl; 1,2-dithio-5-21; a tetrahydro-thiophene-1,1-dioxide; 2-chloro-6-pyridinyl,1,2-dihydro-1,6-dimethyl-2-oxo-4-pyridinyl with a provision that the term Q is S when Het represents 2-pyridinyl-N-oxide.

2. A herbicidal compound as defined in claim 1, wherein Q is O.

3. A herbicidal compound as defined in claim 1, wherein Het is: ##STR120##

4. A herbicidal compound as defined in claim 1, wherein Het is: ##STR121##

5. A herbicidal compound as defined in claim 2, wherein Het is: ##STR122##

6. A herbicidal compound as defined in claim 2, wherein Het is: ##STR123##

7. A herbicidal compound as defined in claim 2, wherein Het is: ##STR124##

8. A herbicidal compound as defined in claim 2, wherein Het is: ##STR125##

9. A herbicidal compound as defined in claim 1, wherein Q is S and Het is: ##STR126##

10. A herbicidal compound as defined in claim 1, wherein Q is S and Het is: ##STR127##

11. A herbicidal compound as defined in claim 1, wherein Q is S and Het is: ##STR128##

12. A herbicidal compound as defined in claim 1, wherein Q is S and Het is: ##STR129##

13. A herbicidal composition comprising a herbicidally effective amount of a compound according to claim 1 and a carrier therefor.

14. A herbicidal comprising a herbicidally effective amount of a compound according to claim 3 and a carrier therefor.

15. A herbicidal comprising a herbicidally effective amount of a compound according to claim 5 and a carrier therefor.

16. A method for combatting undesirable herbs which comprises contacting them with a herbicidally effective amount of a compound according to claim 1.

17. A herbicidal composition comprising a herbicidally effective amount of a compound according to claim 4 and a carrier therefore.

18. A method for combatting undesirable herbs which comprises contacting them with a herbicidally effective amount of a compound according to claim 4.

19. A method for combatting undesirable herbs which comprises contacting them with a herbicidally effective amount of a compound according to claim 3.

20. A method for combatting undesirable herbs which comprises contacting them with a herbicidally effective amount of a compound according to claim 5.